Lodging Image

Surry Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Surry holiday rentals

A two-story house with a front porch, a staircase, and a small garden area.

1. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (9 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is AU$244
includes taxes & fees
19 Oct - 20 Oct
Central Large 2-bedrooms with office in Keene
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

2. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AU$674
includes taxes & fees
19 Oct - 20 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A garden with a wooden pergola, purple flowers, and a river view.

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is AU$369
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

4. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is AU$527
includes taxes & fees
15 Oct - 16 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A rustic cabin with a covered porch, a small shed, and outdoor seating.

5. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AU$229
includes taxes & fees
26 Oct - 27 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

6. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AU$152
includes taxes & fees
30 Oct - 31 Oct
Cozy Vermont Tiny Home Get Away
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

7. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is AU$410
includes taxes & fees
3 Nov - 4 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A lakeside park with picnic tables and a concrete walkway.

8. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is AU$119
includes taxes & fees
15 Oct - 16 Oct
2 private mountain RV pads for rent. Full hook ups
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

9. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (4 reviews)
"The property was adorable, clean and had everything we needed. Even though it rained all weekend we still had the best time. Great, private location with amazing views and close to downtown Keene. The host was very responsive and made sure we were comfortable and had all the info we needed."
United States
Marie M.
The price is AU$415
includes taxes & fees
15 Oct - 16 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

10. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is AU$913
includes taxes & fees
15 Oct - 16 Oct
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A red house with a covered porch and a chimney.

11. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (173 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is AU$514
includes taxes & fees
19 Oct - 20 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

12. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is AU$591
includes taxes & fees
2 Nov - 3 Nov
Lakefront Family Fun Retreat
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

13. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is AU$442
includes taxes & fees
8 Nov - 9 Nov
Cozy Tiny House on Main Street. Fully Renovated.
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

14. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (12 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is AU$216
includes taxes & fees
26 Oct - 27 Oct
Yurt Oasis in the woods of Hinsdale, NH
A modern living room with a flat-screen TV, a sectional sofa, a coffee table, and a large window providing a view of the outdoors.

15. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
10.0 out of 10, Exceptional, (11 reviews)
"Great place to relax with a woody vibe. Excellent stay"
United States
Logan V.
The price is AU$989
includes taxes & fees
18 Oct - 19 Oct
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Dining

16. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is AU$594
includes taxes & fees
5 Nov - 6 Nov
Charming Chester Farmhouse near Near VT Slopes
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Surry Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"They are right downtown with parking so, unlike other hotels in Brattleboro, guests can walk to local restaurants and attractions in this chrarming river town."
rollin 1-night trip
Posted 5 hours ago
Latchis Hotel

Find out more about Surry

Everything you need to know about Surry holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Surry holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Surry holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Surry holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Surry. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Surry holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Surry holiday rentals we have selected for you start as low as AU$216 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Surry rentals

At Expedia, we put the best Surry holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Surry rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Surry holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Surry. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Surry?

Yes, there are holiday rentals close to the most popular sights in Surry, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Surry has to offer?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Surry is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Surry?

While exploring the area, visit family-friendly sights like Cheshire Children's Museum, or get outside and enjoy nature at Ashuelot River. In the wider area, you’ll find Brentwood Golf Course and Alumni Field.

What’s a holiday rental in Surry like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Surry. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips.