A pebbled beach with a sunset and a distant bridge.

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21 Sept - 22 Sept
Tomorrow
22 Sept - 23 Sept
This weekend
25 Sept - 27 Sept
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2 Oct - 4 Oct

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Our top choices for Shelter Island Heights hotels

1. The Chequit

The Chequit
The Heights
United States
Kristin
£162
includes taxes & fees
5 Oct - 6 Oct
The Chequit

2. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
£184
includes taxes & fees
5 Oct - 6 Oct
House on Chase Creek

3. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
£172
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House

4. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
£267
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse

5. Zey Hotel

Zey Hotel
Greenport
United States
Renee
£144
includes taxes & fees
27 Sept - 28 Sept
Zey Hotel

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
£236
includes taxes & fees
21 Oct - 22 Oct
Silver Sands Motel & Beach Bungalows

7. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Jordan
£218
includes taxes & fees
15 Oct - 16 Oct
The Harbor Front Inn

8. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
£234
includes taxes & fees
22 Sept - 23 Sept
American Beech Hotel

9. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
£228
includes taxes & fees
14 Oct - 15 Oct
Sound View Greenport

10. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
£191
includes taxes & fees
1 Oct - 2 Oct
The Shoals Suites and Slips

11. North Fork Resort

North Fork Resort
Greenport
United States
Harold
£244
includes taxes & fees
21 Oct - 22 Oct
North Fork Resort

12. The Menhaden

The Menhaden
Greenport
United States
Lisa
£344
includes taxes & fees
7 Oct - 8 Oct
The Menhaden

13. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
£294
includes taxes & fees
5 Oct - 6 Oct
Oyster Estate

14. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
£318
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums

15. Clinton Motel

Clinton Motel
Clinton
United States
Selena
£67
includes taxes & fees
22 Sept - 23 Sept
Clinton Motel

16. Hamlet Inn

Hamlet Inn
Southampton
United States
Thomas
£122
includes taxes & fees
22 Sept - 23 Sept
Hamlet Inn

17. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
£69
includes taxes & fees
8 Oct - 9 Oct
Pier Blue Inn Old Saybrook - Essex

18. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
£276
includes taxes & fees
4 Oct - 5 Oct
Sag Harbor Inn

19. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Michael
£87
includes taxes & fees
12 Oct - 13 Oct
Quality Inn Old Saybrook - Westbrook

20. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
£125
includes taxes & fees
19 Oct - 20 Oct
The Bentley Hotel Southampton
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Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas for the activities you enjoy most.

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

Hay Beach

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
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Menhadden Lane Beach

8.8/10 (3 reviews)
Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
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Shelter Island Country Club

10.0/10 (3 reviews)
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
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Sylvester Manor

8.8/10 (3 reviews)
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
See properties

Learn more about Shelter Island Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

See all hotels in Shelter Island Heights
A pebbled beach with a sunset and a distant bridge.

Top Shelter Island Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The grounds and the interior of the property were beautifully maintained and tastefully appointed. The staff is exceptionally friendly. The bathroom in my room was dated and needed remodeling. Wall dispensers of shampoo, conditioner and body wash were not installed in shower as is generally offered in most 4 star hotels. While there is a coffee machine in guest rooms, there is no complimentary coffee offered in the lobby."
Russell 1-night trip
Posted 14 hours ago
Water's Edge Resort & Spa
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"All good, however booking through Expedia cost me 300$ more than me booking straight with hotel… service fees at hotel as well…"
Jude 2-night trip
Posted 18 hours ago
Ocean Surf Resort
Offshore Montauk

Offshore Montauk

10/10 Excellent
"Beautiful location !! Room was very clean and beautiful as well!!"
Lisa 2-night trip
Posted 22 hours ago
Offshore Montauk
Ocean Resort Inn

Ocean Resort Inn

8/10 Good
"Small but well maintained room. Great location close to the beach and downtown."
Edward 3-night trip
Posted 3 days ago
Ocean Resort Inn

More cheap stays in Shelter Island Heights

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
£69
8 Oct - 9 Oct
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
£76
29 Sept - 30 Sept
includes taxes & fees
Budget Host East End
Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
£103
1 Oct - 2 Oct
includes taxes & fees
8.4/10 Very good! (969 reviews)
Kenny's Tipperary Inn
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
£117
29 Sept - 30 Sept
includes taxes & fees
8.6/10 Excellent! (321 reviews)
Ocean Surf Resort
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
£120
1 Oct - 2 Oct
includes taxes & fees
The Atlantic Hotel
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
£140
20 Oct - 21 Oct
includes taxes & fees
Montauk Blue Hotel

Find out more about Shelter Island Heights

Top reasons to visit Shelter Island Heights

  • Scenic Outdoor Activities: Shelter Island Heights offers a variety of outdoor pursuits, including golf and recreational hiking, perfect for nature enthusiasts.
  • Historic Charm: Explore the quaint historic district featuring attractions like the Presbyterian Church, highlighting the area's rich heritage.
  • Beautiful Beaches: Enjoy stunning beaches that provide a serene environment for relaxation and water activities.
  • Diverse Accommodation: Choose from a range of lodgings, including pet-friendly and family-friendly options, catering to all types of travellers.
  • Tranquil Atmosphere: Immerse yourself in the peaceful surroundings and welcoming community, ideal for romantic getaways.

Find great hotels near Shelter Island Heights

For an enchanting getaway in Shelter Island Heights, you'll discover a delightful selection of hotels and agritourism properties. Whether you seek a pet-friendly establishment or family-friendly accommodations, this charming destination caters to all travellers. Enjoy the unique experience of Shelter Island Heights, where you can relax in comfortable lodgings while immersing yourself in the picturesque surroundings and adventure-filled activities.

  • Sound View Greenport: Sound View Greenport is a delightful 3.5-star hotel boasting a guest rating of 8.4, situated 3.2km from Shelter Island Heights. This charming property is ideal for families and pet owners seeking a beach getaway. Guests can enjoy direct access to the beach, making it perfect for sun-soaked days by the sea. Amenities for children, such as free cribs and window guards, ensure a family-friendly atmosphere. The hotel also accommodates pets, with specific policies in place for dogs and cats. This tranquil retreat combines relaxation with family-oriented features for a memorable stay.
  • Sag Harbor Inn: Sag Harbor Inn, a 3.5-star establishment with a remarkable guest rating of 9.4, is located 9.7km from Shelter Island Heights. This hotel presents an excellent choice for business travellers, offering a serene environment conducive to work and relaxation. With its tasteful decor and comfortable accommodations, guests can enjoy a peaceful retreat after a busy day. The inn's prime location allows easy access to local attractions, ensuring that both business and leisure needs are met seamlessly. A stay here promises a blend of professionalism and comfort.
  • The Harbor Front Inn: The Harbor Front Inn is another 3.5-star option, featuring a commendable guest rating of 8.8, just 1.6km from Shelter Island Heights. This inn is perfect for both business travellers and pet owners, allowing pets on-site with specific policies for dogs. With its waterfront location, guests can appreciate stunning views while enjoying a comfortable and relaxing atmosphere. The inn's amenities cater to a range of needs, ensuring a pleasant stay for all. Whether for work or leisure, this property provides an inviting and accommodating experience.

Where to stay near Shelter Island Heights

Discover the charm of Shelter Island Heights, an idyllic destination perfect for outdoor adventures, family getaways, and romantic escapes. Immerse yourself in the stunning scenery and welcoming island community, with a variety of excursions to enjoy. Nearby attractions offer a blend of luxury and budget-friendly experiences, making it a lovely spot for every traveller. Explore the unique neighbourhoods around Shelter Island Heights, and embrace the serene atmosphere this enchanting location has to offer.

  • Hamptons: Located approximately 16.1km from Shelter Island Heights, the Hamptons is a renowned getaway for those seeking a beachside retreat. With a vibrant seasonal influx of visitors peaking from June to August, this area is perfect for romantic escapades and outdoor adventures. Explore beautiful beaches, play a round of golf, or enjoy the ski fields during the colder months. Local landmarks such as family-friendly beaches and picturesque lakes offer a perfect backdrop for relaxation and leisure.
  • Greenport: Just 1.6km away from Shelter Island Heights, Greenport is a charming city that captures the essence of coastal living. Its seasonal tourism peaks in the summer months, making it ideal for outdoor enthusiasts and couples alike. Enjoy a variety of activities, from golfing to attending lively music concerts. With lovely parks and family beaches nearby, Greenport is a delightful spot to unwind and soak up the sun, offering a blend of relaxation and entertainment.
  • Noyack: Nestled 9.7km from Shelter Island Heights, Noyack is a quaint village known for its stunning natural beauty. This area also experiences moderately seasonal visitor numbers, with peak travel during the summer. Noyack invites travellers to indulge in outdoor activities, from golfing to enjoying its scenic beaches. With family beaches and serene lakes in the vicinity, visitors can relish the romantic atmosphere and picturesque views that make Noyack an enchanting destination.

Things to do in Shelter Island Heights

Shelter Island Heights is an idyllic destination for outdoor enthusiasts and families alike, perfect for a romantic getaway. Visitors can enjoy a round of golf at the local course, explore the scenic recreational areas, and take in the tranquil surroundings. Whether you're seeking relaxation or adventure, this charming locale offers a delightful array of activities to create lasting memories.

Shopping

In Shelter Island Heights, you can enjoy quaint shops offering local crafts and souvenirs. If you're up for a drive, check out the nearby Greenport Village, home to charming boutiques and unique gift shops, or head to the Tanger Outlets in Riverhead for a larger selection.

Recreation

At the Shelter Island Heights Spa, indulge in rejuvenating treatments that incorporate local ingredients, surrounded by tranquil gardens. For a unique experience, visit the nearby Yoga Retreat, where you can partake in outdoor classes with stunning views of the water, promoting both relaxation and mindfulness.

Adventure

Explore the breathtaking landscapes of Shelter Island Heights by kayaking in the tranquil waters of Dering Harbor, where you can encounter local wildlife. For hiking enthusiasts, the picturesque trails of Mashomack Preserve offer scenic views and a chance to immerse yourself in nature’s beauty.

Nightlife

Experience the vibrant nightlife at The Islander on Shelter Island Avenue, where you can enjoy cocktails and local brews. For a more relaxed vibe, visit the Shelter Island Heights Pavilion, offering live music and a charming atmosphere to unwind after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Shelter Island Heights

  • The most and least expensive months on average to stay in a hotel: The hotel pricing in Shelter Island Heights is moderately seasonal. The cheapest months to stay in Shelter Island Heights are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shelter Island Heights is Tuesday. The most expensive day to stay in Shelter Island Heights is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as budget, desired location, and preferred type of accommodation. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Shelter Island Heights with your flights and activities by opting for an Expedia package.

Find the best attractions near Shelter Island Heights

Ideal for outdoor, family, and romantic getaways, Shelter Island Heights boasts attractions like the historic district, Presbyterian Church, and nearby Fishers Island. Enjoy beautiful beaches, explore urban parks, and immerse yourself in local culture. With a variety of activities catering to diverse interests, visitors can relish the area's charm while soaking up the scenic beauty and rich history.

  • East Hampton Main Beach: Experience the quintessential beach vibes at East Hampton Main Beach, located 20.9km from Shelter Island Heights. This stunning stretch of sand offers sunbathing, swimming, and picturesque views, perfect for a relaxing day by the ocean.
  • Orient Point County Park: Just 12.9km away, Orient Point County Park is an urban oasis ideal for families. Enjoy outdoor activities such as picnicking, hiking, and birdwatching amidst beautiful natural surroundings, making it a great spot for a day out.
  • Gardiner's Bay Country Club: Located a mere 3.2km from Shelter Island Heights, Gardiner's Bay Country Club offers a premier golfing experience. Enjoy well-maintained greens and stunning bay views, making it a must-visit for golf enthusiasts.

Best time to go to Shelter Island Heights

The best time to visit Shelter Island Heights is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyLowModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyHighAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyAverageModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

The nearest major airports for your trip to Shelter Island Heights

Accessing Shelter Island Heights is convenient via three major airports. New York, NY (JFK) is approximately 130.4km away, with nearby hotels such as the 5-star Arlo Williamsburg and The William Vale, both situated 17.7km from the airport. LaGuardia Airport (LGA), located around 132.0km from Shelter Island Heights, offers luxurious accommodations like The Plaza - A Fairmont Managed Hotel and The Pierre, both 5-star options just 8.0km away. Alternatively, Hartford, CT (BDL) is about 98.2km from your destination, with good hotel choices like the 4-star DoubleTree by Hilton Hartford, just 1.6km from the airport.

Frequently asked questions

What is the best area to stay in Shelter Island Heights?
The best area to stay in Shelter Island Heights is the village area itself, particularly around the historic Shelter Island Heights Historic District.This district is the heart of the community, characterised by its historic Victorian homes and tree-lined streets. It's where you'll find most of the island's amenities, including shops, restaurants, and the ferry terminal for easy access to Greenport. The area is very walkable, making it convenient to explore on foot.For couples seeking a relaxing getaway, staying within the historic district offers a quintessential island experience. You'll be close to dining options and can enjoy strolls along the streets admiring the architecture, or head down to Crescent Beach for a peaceful afternoon by the water. Many accommodations here offer a more intimate setting great for two.Families often find the historic district appealing due to its proximity to activities. The village green provides open space for children, and the calm waters of Crescent Beach are suitable for swimming and building sandcastles.
What are the best hotels in Shelter Island Heights that travellers recommend?
One of the best hotels in Shelter Island Heights that travellers recommend is The Pridwin Hotel.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, offers a wonderful experience with its private beach access and a refreshing poolside bar. Guests frequently highlight the beautiful and clean rooms, the amazing amenities, and the great facilities. Many rooms boast breathtaking water and ocean views, and premium bedding and bathrobes add to the comfort. The hotel is conveniently located just 0.4 km from Crescent Beach and 0.9 km from Sunset Beach, making it ideal for beach enthusiasts.
What are the best family hotels in Shelter Island Heights?
For families visiting Shelter Island Heights, The Pridwin Hotel and The Rams Head Inn are both excellent choices.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, is a fantastic option for families. Guests frequently highlight the beautiful and clean rooms, amazing amenities, and great facilities. Families will appreciate amenities such as sofa beds, kids' meals, and a pool with a gate for added safety. Many rooms offer water or ocean views, adding to the relaxing experience. The hotel is also conveniently located near Sunset Beach, just 0.9 km away, and Crescent Beach, a mere 0.4 km away.Another good option is the 4-star Rams Head Inn, rated 7.6. This hotel caters well to families, offering books and games for children, as well as highchairs. Guests can also enjoy a complimentary continental breakfast. It is located 2.5 km from Menhadden Lane Beach.
What are the best spa hotels in Shelter Island Heights?
For a top-tier spa experience in Shelter Island Heights, The Pridwin Hotel is an excellent choice.This 4-star hotel, boasting an impressive 9.6 rating, offers a full-service onsite spa that provides a wide range of treatments, including Swedish massage, deep tissue massage, body wraps, body scrubs, and hydrotherapy treatments. Guests can also enjoy facial treatments, manicures, pedicures, and a steam room. The Pridwin Hotel is conveniently located just 0.4 km from Crescent Beach and 1.6 km from Shelter Island Country Club, making it ideal for those who appreciate beautiful surroundings and nearby recreational activities. Guests frequently praise its beautiful and clean rooms, amazing amenities, great facilities, and delicious food.
What hotels in Shelter Island Heights offer free breakfast?
For hotels in Shelter Island Heights that offer complimentary breakfast, consider The Pridwin Hotel and The Rams Head Inn.The 4-star Pridwin Hotel, with an outstanding 9.6 rating, offers both free breakfast and continental breakfast. Guests frequently mention the beautiful, clean rooms, amazing amenities, and delicious food. This hotel also provides a free ferry terminal shuttle, free self-parking, and free WiFi. It boasts lovely water and ocean views and is conveniently located near Sunset Beach, just 0.9 km away, and Crescent Beach, 0.4 km away.Another option is the 4-star Rams Head Inn, rated 7.6, which also provides free breakfast and continental breakfast. This hotel offers free WiFi, free self-parking, and is situated approximately 2.5 km from Menhadden Lane Beach.
What are the top pet-friendly hotels in Shelter Island Heights?
For top pet-friendly accommodation in Shelter Island Heights, consider The Rams Head Inn.The 4-star Rams Head Inn, with a rating of 7.6, warmly welcomes pets, specifically dogs. This charming inn offers a delightful dining experience for couples and is conveniently located just 2.5 kilometres from Menhadden Lane Beach.
What are the most romantic hotels in Shelter Island Heights for couples?
For a romantic getaway in Shelter Island Heights, couples should consider The Pridwin Hotel or The Rams Head Inn.The 4-star Pridwin Hotel, with an impressive 9.6 rating, is a beautiful option. Guests frequently praise its amazing amenities, great facilities, and delicious food. Many rooms offer lovely water or ocean views, and the hotel provides complimentary breakfast, including a continental option, and free toiletries. It is conveniently located just 0.4 km from Crescent Beach and 1.6 km from Shelter Island Country Club, making it easy to explore the surroundings.Another option is the 4-star Rams Head Inn, rated 7.6, which features couples' dining. This hotel offers complimentary continental breakfast and free toiletries, along with free self-parking. It is located 2.5 km from Menhadden Lane Beach, providing a quiet setting for a romantic escape.
What are the best hotels in Shelter Island Heights near Crescent Beach?
For hotels in Shelter Island Heights near Crescent Beach, The Pridwin Hotel is an excellent choice.The 4-star Pridwin Hotel, with an impressive rating of 9.6, is located just 0.4 km from Crescent Beach. Guests consistently praise its beautiful and clean rooms, amazing amenities, and great facilities. The hotel also boasts delightful food, and its location is frequently highlighted as a major positive. Many rooms offer water or ocean views, and there is a pool available.
When is the best time to go to Shelter Island Heights?
The best time to go to Shelter Island Heights is during the summer months, from June to September, when the weather is warm and the island is fully operational.During this period, all the island's amenities, including restaurants, shops, and recreational activities, are open and readily available. The ferry service also runs more frequently, making travel to and from the island very convenient. This time of year is superb for those looking to enjoy the beaches and outdoor activities.For those who prefer a quieter experience with pleasant weather, late spring (May) and early autumn (October) are also excellent choices. The crowds are smaller, but the weather is still generally mild enough to enjoy walking, cycling, and the island's natural beauty.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shelter Island Heights.
How much is the nightly rate at a Shelter Island Heights hotel?
Prices for hotels in Shelter Island Heights often vary, but you can find a great deal from £67 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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