Vineyard Holidays from £812

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Your Vineyard Holiday

Reserving a Vineyard holiday package is a good way to get to know this unique neighbourhood. From its well-known places to its little-known gems, there's plenty to discover. Kick start your trip to Vineyard by checking out nearby attractions such as Sint Maarten Park, Little Bay Beach and Guana Bay Beach. No matter what your dream Vineyard holiday may look like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
per person
17 Sept - 22 Sept
found 19 hours ago
Return flight included
London (LGW) to Philipsburg (SXM)
9/10 Wonderful! (1,192 reviews)
The staff were friendly. Check in was quick and smooth and the wait time for our room was minimal. I especially loved that there was house keeping every day.

Reviewed on 3 Aug 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
per person
13 Sept - 20 Sept
found 19 hours ago
Return direct flight included
Manchester (MAN) to Philipsburg (SXM)
9.2/10 Wonderful! (1,192 reviews)
Everything was great, quiet, safe. 3 pools to choose and love to walk around the neighborhood

Reviewed on 2 Aug 2025

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
per person
4 Oct - 10 Oct
found 1 hour ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9/10 Wonderful! (1,733 reviews)
Convenient, but crowded area, great for young adults

Reviewed on 2 Aug 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
9.2/10 Wonderful! (946 reviews)
Wonderful customer service

Reviewed on 3 Aug 2025

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LON) to Philipsburg (SXM)
8.4/10 Very Good! (1,003 reviews)
Location was excellent! Snorkeling was fantastic right off the beach. Ft. Amsterdam was beautiful! This place is perfect. I opted for all inclusive. If you’re not drinking it’s not worth the price.

Reviewed on 2 Aug 2025

Where to stay in Vineyard

Find the best Vineyard areas and neighborhoods for the activities you enjoy most. Learn more about Vineyard
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Indigo Bay

If you're looking for some top things to see and do in Indigo Bay and surrounding area, you can visit Little Bay Beach and Indigo Beach.

Find hotels in Indigo Bay

Top hotels in Vineyard

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
The price is £213 per night from 18 Aug to 19 Aug
£213
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (2,449 reviews)
"The rooms were very clean, the buffet had a lot of variety. Staff very friendly"

Reviewed on 31 Jul 2025

Sonesta Maho Beach All Inclusive Resort Casino & Spa
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is £207 per night from 5 Aug to 6 Aug
£207
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (1,788 reviews)
"Convenient, but crowded area, great for young adults"

Reviewed on 2 Aug 2025

The Morgan Resort Spa Village
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37, Simpson Bay
Fully refundableReserve now, pay when you stay
The price is £59 per night from 20 Aug to 21 Aug
£59
20 Aug - 21 Aug
includes taxes & fees
8.8/10 Excellent! (1,261 reviews)
"Beautiful location, rooms are spacious and food was AMAZING!"

Reviewed on 31 Jul 2025

Simpson Bay Resort, Marina & Spa
See all 3,588 properties in Vineyard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Vineyard travel package cost?
Explore the best of Vineyard from as low as £812. We offer a great selection of hotels, flights and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of experiences or tours to your travel package.
If I'm not able to travel, can I cancel my Vineyard travel package?
Don't stress if you're rethinking your Vineyard travel package — it's possible to change or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally get that life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Vineyard?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got it all. Choose a combination that suits your style and see your savings pile up. We know a package deal is never a one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options worldwide, which lets you customize your Vineyard adventure.
Does Expedia offer Book Now, Pay Later Vineyard holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has worked out a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a dream getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If making small repayments each month works for you, pick this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday in multiple transactions.
  • Low deposit holidays: When you stumble on an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in Vineyard?
Vineyard has a number of interesting places to explore, such as Guana Bay Beach. Book a hotel near this attraction and make sightseeing a breeze.
What are the top hotels in Vineyard?
Reserve a room at Princess Heights Luxury Boutique Condo Hotel. It's one of this area's most in-demand properties. Another top-rated option in Vineyard is Oyster Bay Beach Resort.
How far in advance should I book my Vineyard holiday?
While prices fluctuate, we generally advise booking your holiday as soon as possible. Many international airfares become available on Expedia up to 12 months in advance. If you're booking last minute, you might still be lucky. Discount prices to Vineyard sometimes appear only weeks before departure.
What does an Expedia Vineyard travel package include?
It all comes down to what sort of trip you have in the works. Vineyard travel deals can include hotels, car rentals and flights. You can mix and match to create the package that suits your budget and style. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a Vineyard travel package?
Bundling your bookings into a Vineyard travel package is the easiest way to organise your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Vineyard Expedia travel package?
Yes — that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 airline partners worldwide, so you have options galore when creating your Vineyard trip.

Popular places to visit

Great Bay Beach

Great Bay Beach

4.5/5(2 reviews)

If a restful holiday is part of your travel plans, Great Bay Beach might be the perfect place to visit during your trip to Philipsburg. Visit the shops and top-notch restaurants in this romantic area.

Great Bay Beach
Guana Bay Beach showing cuddly or friendly animals, a coastal town and a beach

Guana Bay Beach

4/5(1 review)

The picturesque shores of this tranquil bay provide a great opportunity to escape the crowds and jump in the crystal clear water for surfing or swimming.

Guana Bay Beach

Little Bay Beach

If a restful holiday is part of your travel plans, Little Bay Beach might be the perfect place to visit during your trip to Philipsburg. Amble around this romantic area's seaside and enjoy its top-notch restaurants.

Little Bay Beach

Things to do

Sky Explorer and Flying Dutchman

Sky Explorer and Flying Dutchman

£69
per adult
74% of travellers recommend
Sky Explorer and Flying Dutchman
Tango Sunset Dinner Cruise

Tango Sunset Cruise with Caribbean Dinner & Open Bar

£63
per adult
94% of travellers recommend
Tango Sunset Cruise with Caribbean Dinner & Open Bar
Sand Dollar Snorkeling Adventure

Half Day Snorkeling Adventure

£48
per adult
100% of travellers recommend
Half Day Snorkeling Adventure
See all activities in Philipsburg

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.