Woodstock Holidays from £651

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Your Woodstock Holiday

Prepare to experience Woodstock on your terms with a custom Woodstock holiday package! Uncovering the best parts of this interesting city is simple with a base in a neighbourhood such as Killingly, which is good for nature, among other things. Every trip to Woodstock needs a well-thought-out itinerary. Fill yours with famous sights like Taylor Brooke Winery, Little River Plaza Shopping Centre and Harrisville Golf Course. Don't delay visiting this destination any longer. The perfect Woodstock holiday is only a few clicks away with Expedia.

The Latest Woodstock Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Groton/Mystic

Baymont by Wyndham Groton/Mystic

2.5 out of 5
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Providence (PVD)
6.4/10 (1,011 reviews)
Rooms were always clean and in good condition when we came in after our days out. Housekeeping staff were very responsive to requests. However, sign outside property states that there is free breakfast and dinner for guests which is slightly misleading. The WiFi was questionable as well, as we lost signal several times but were able to get it back by restarting our devices. Overall we liked our stay. We'd definitely stay again.

Reviewed on 15 Jun 2025

Pleasant View Inn

Pleasant View Inn

3 out of 5
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return flight included
London (LON) to Providence (PVD)
8/10 Very Good! (1,005 reviews)
Location, location , location and nice staff . Very basic property w a fabulous ocean front view . Carpets could use cleaning or replacing . Bath towels are very skimpy .

Reviewed on 23 Jun 2025

The Atlantic Inn

The Atlantic Inn

3.5 out of 5
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return flight included
London (LON) to Providence (PVD)
9.6/10 Exceptional! (71 reviews)
Beautiful property wonderful rooms great stay!!

Reviewed on 22 Jun 2025

Sea Shell Motel

Sea Shell Motel

2 out of 5
per person
15 Sept - 22 Sept
found 1 day ago
Return flight included
London (LON) to Providence (PVD)
8/10 Very Good! (12 reviews)
Owner was very nice and attentive to our needs with anything else we needed. Quiet backyard with grill picnic tables and kayaks for use on salt pond. Rooms are a little tight, but for 4 people suggest going to beach ball inn across the street there sister property. Alot more room in there 2 bedrooms.

Reviewed on 22 Jun 2025

The Taber Inne & Suites

The Taber Inne & Suites

2 out of 5
per person
15 Sept - 22 Sept
found 1 day ago
Return flight included
London (LON) to Providence (PVD)
9.4/10 Exceptional! (1,004 reviews)
Great location and nice property. Staff was very friendly and helpful. Would definitely stay again.

Reviewed on 24 Jun 2025

Sandy Shore Motel

Sandy Shore Motel

2.5 out of 5
per person
15 Sept - 22 Sept
found 1 day ago
Return flight included
London (LON) to Providence (PVD)
8/10 Very Good! (406 reviews)
The staff were so nice and accommodating. The property is standard beach front motel, clean and safe place to rest for the noghtz

Reviewed on 25 Jun 2025

Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Taylor Brooke Winery, Roseland Park Golf Course and Woodstock Golf Course

Our pick of the best Woodstock Hotel Deals

Secluded 2-Acre Lakefront Home! Book Your Retreat!
Secluded 2-Acre Lakefront Home! Book Your Retreat!
Woodstock, CT
Stay at this holiday home in Woodstock. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Black Pond and Campert Preserve are located ...
9.8/10 Exceptional! (65 reviews)
Just what we needed
"The property is very nice and roomy. If you have a big family like ours and you need a place in this part of CT, you’re in luck."

Reviewed on 21 Jun 2025

Secluded 2-Acre Lakefront Home! Book Your Retreat!
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Woodstock, CT
Stay at this apartment in Woodstock. Enjoy free Wi-Fi, an in-room coffee maker and air conditioning. Popular attractions May Memorial Library and North Woodstock ...
10/10 Exceptional! (4 reviews)
"It was absolutely beautiful! Very clean and exactly like the photos. Super quiet and peaceful. The only issues were needing a boost to get in the bed because they are high and im quite short. A stool would be helpful. And the shower is quite small but we made it work. The stay was so great we didn't ..."

Reviewed on 16 Jun 2025

Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Stay at this 3-star business-friendly hotel in Southbridge. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,195 reviews)
"The hotel itself was beautiful and clean and the staff were amazing. The bartender (sorry that I don’t remember her name) made the most delicious rum and juice drink I’ve ever had. The immediate area around the hotel is less impressive, but we never felt unsafe."

Reviewed on 23 Jun 2025

Wellsworth Hotel
See all 279 properties in Woodstock
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 Woodstock travel package cost?
From as low as £651. Yes, you read that right. Our Woodstock packages are an easy way to make your budget stretch further. Bundle your flights, hotels and rental car and discover this lively destination.
If I'm not able to travel, can I cancel my Woodstock travel package?
We totally understand --- life can throw you the odd curveball. If you've locked in a Woodstock travel package and need to change or cancel it, we can help. We recommend checking out our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to cancel and rebook free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to Woodstock?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities --- we've got everything you need. Pick and choose the combination that best suits you and watch your savings grow. We know a travel package is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options globally, which lets you customize your Woodstock adventure.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Expedia has teamed up with online lender Klarna to make your next trip easier on your budget. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Check out these flexible payment options:
  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you spot an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Woodstock?
A trip to Woodstock wouldn't be complete without paying a visit to Woodstock Golf Course, Roseland Park Golf Course and Harrisville Golf Course. Stay near these sights and make sightseeing a breeze.
What are the top hotels in Woodstock?
Get your holiday off to a great start by locking in a room at La Quinta Inn & Suites by Wyndham Norwich-Plainfield-Casino. It's one of most popular properties in Woodstock. Another comfortable option is Comfort Inn & Suites.
How far in advance should I book my Woodstock holiday?
It can be difficult to know when is the perfect time to book your trip to Woodstock. But generally the earlier you book, the lower the prices. In some cases, you can lock in your flights and hotels nearly 12 months before your departure date. If you're considering a last-minute getaway, no need to stress! There are fantastic deals advertised on Expedia every single day.
What does an Expedia Woodstock travel package include?
Hotels, flights and rental cars, or any combination of them --- it's up to you! Whether you're exploring Woodstock with the family or travelling by yourself, there's a bundle to suit your budget and style. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking a Woodstock travel package?
A package can be more affordable than separately booking all you need for your adventure. For example, bundle your flights, hotels and rental cars and save big. Whatever kind of holiday you're planning, there's bound to be a package that's right for you.
Can I choose my airline with a Woodstock Expedia travel package?
Expedia has access to more than 550 partner airlines globally, so you definitely can. Just select the carrier you want and craft your ideal Woodstock holiday.

Discover the most popular places to visit in Woodstock

Taylor Brooke Winery

You can enjoy a tasting or tour at Taylor Brooke Winery during your travels to Woodstock. While in this family-friendly area, you can savour the top-notch restaurants.

Taylor Brooke Winery

* 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.