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Surry Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (8 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is HK$1,236
HK$1,511 total
includes taxes & fees
4 Oct - 5 Oct
Central Large 2-bedrooms with office in Keene
A garden with a wooden pergola, purple flowers, and a river view.

2. 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 HK$1,045
HK$2,067 total
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

3. 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 HK$1,506
HK$3,788 total
includes taxes & fees
1 Oct - 2 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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 HK$1,797
HK$3,158 total
includes taxes & fees
22 Oct - 23 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 HK$706
HK$1,234 total
includes taxes & fees
5 Oct - 6 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

6. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,182
HK$4,589 total
includes taxes & fees
8 Oct - 9 Oct
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A lakeside park with picnic tables and a concrete walkway.

7. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$432
HK$639 total
includes taxes & fees
1 Oct - 2 Oct
2 private mountain RV pads for rent. Full hook ups
A red house with a covered porch and a chimney.

8. 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, (172 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 HK$1,334
HK$2,900 total
includes taxes & fees
7 Oct - 8 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A covered outdoor seating area with a sofa, cushions, a table, and a lantern.

9. Modern 6BR Home for Large Groups & Families

Modern 6BR Home for Large Groups & Families
Keene
8.0 out of 10, Very good, (2 reviews)
"Nice location, with lots of space. Beds were comfy and my shower was nice a warm. Thankyou"
United States
Sheryl M.
The price is HK$3,019
HK$6,570 total
includes taxes & fees
4 Oct - 5 Oct
Modern 6BR Home for Large Groups & Families
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

10. 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 HK$1,334
HK$2,329 total
includes taxes & fees
20 Oct - 21 Oct
Wellness Getaway with a Personal Sauna, and Private River Beach!
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

11. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (10 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 HK$678
HK$1,161 total
includes taxes & fees
5 Oct - 6 Oct
Yurt Oasis in the woods of Hinsdale, NH
A room with white paneled walls, a wooden bench, a teal cushion, a vase with flowers, a framed picture, and a shelf with books and a small electronic device.

12. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is HK$593
HK$848 total
includes taxes & fees
31 Oct - 1 Nov
Cozy Vermont Tiny Home Get Away
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

13. 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 HK$1,177
HK$3,533 total
includes taxes & fees
21 Oct - 22 Oct
Lakefront Family Fun Retreat
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

14. 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 HK$2,648
HK$4,925 total
includes taxes & fees
2 Oct - 3 Oct
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

15. 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, (1 review)
"This place was really beautifully appointed and thoughtfully stocked. Kitchen stock was great.Lots of coffees, teas, bottled water…all very thoughtful touches. Comfy beds. Beautiful little home. Pond was really nice. Convenient to Monandock. Really loved it. Lots of appreciation for the hosts."
United States
Len S.
The price is HK$1,871
HK$2,320 total
includes taxes & fees
1 Oct - 2 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
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 HK$1,640
HK$3,313 total
includes taxes & fees
20 Oct - 21 Oct
Charming Chester Farmhouse near Near VT Slopes
A modern kitchen with a built-in oven, a dining area with a bench, and a view of the adjacent bedroom.

17. 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 HK$3,171
HK$5,322 total
includes taxes & fees
8 Oct - 9 Oct
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
A kitchen with a brick fireplace, wooden cabinets, a central island with stools, and a large window with plants.

18. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
Cobb Meadow House: Cozy 5 Bedroom Retreat
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.
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Top Surry Hotel Reviews

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

8/10 Good
"Great place to stop in and rest your head for the night - Last minute stop, greeted warmly, clean bed, hot shower - What more could you want? Reasonably priced!"
Derek 1-night trip
Posted 4 hours ago
Travelodge by Wyndham Brattleboro VT

Find out more about Surry

Search for holiday rentals in Surry on Expedia! You can easily find your home rentals, villas, holiday apartments in Surry using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Surry while they last

Look no further and take a look at our great range of rental properties in Surry!

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.