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Surry Holiday Rentals

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Our top choices for Surry holiday rentals

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (14)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
The price is NZ$579
includes taxes & fees
17 Dec - 18 Dec
Owl's Nest Treehouse

Holiday Home in Washington

Private Beach And Mountain Lake Home
9.6 out of 10, Exceptional, (124)
"Just returned from a wonderful stay at this property. The house was clean and had everything you could need while on vacation. The pond was so clean and clear. We even saw a loon."
United States
Patricia K.
Private Beach And Mountain Lake Home
10.0 out of 10, Exceptional, (62)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (7)
LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is NZ$636
includes taxes & fees
23 Dec - 24 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
10.0 out of 10, Exceptional, (7)
"Perfect place for a quick getaway! Lovely house in a great location!"
United States
Johnna P.
Direct Waterfront, Year-Round, A-Frame Cabin

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is NZ$654
includes taxes & fees
7 Jan - 8 Jan 2026
Chester Farmhouse Ski Retreat near Slopes
9.8 out of 10, Exceptional, (9)
"Clean, lots of space, helpful host, hot tub was also nice"
United States
Howard H.
The price is NZ$722
includes taxes & fees
18 Dec - 19 Dec
16 ppl 2 hot tubs, game room, fire pit
Enchanting pet-friendly and private cabin with cozy pellet fireplace
Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.
9.4 out of 10, Exceptional, (29)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
United States
Jennifer
Cozy Updated Log Cabin with Mountain Views close to Monadnock
10.0 out of 10, Exceptional, (18)
"The house is absolutely beautiful - Check in super easy"
United States
Dawn J.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is NZ$438
includes taxes & fees
12 Jan - 13 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
10.0 out of 10, Exceptional, (1)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
The price is NZ$795
includes taxes & fees
16 Dec - 17 Dec
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
10.0 out of 10, Exceptional, (128)
"Perfect little vaca cabin. Enjoyed our stay and time on the beach. Will definitely book again. "
United States
Mark K.
Log Home In Secluded Lake Ashuelot Estates
10.0 out of 10, Exceptional, (2)
"This was a great place to disconnect with technology and reconnect with family. We had a great time."
United States
Jackie D.
Lakefront Cabin/ 314` Shoreline

Holiday Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is NZ$481
includes taxes & fees
16 Dec - 17 Dec
Downtown Hot Tub Escape
10.0 out of 10, Exceptional, (2)
"A perfect getaway for a large group of friends getting together for a reunion. Beautiful property and location, and fantastic amenities. Would absolutely recommend and stay again!"
United States
Christian R.
Spacious 7-bedroom cabin in charming Grafton with fitness room, sauna & hot tub
10.0 out of 10, Exceptional, (72)
"The property was absolutely perfect. House was even better than the pictures with so much space to spread out with a large family. It is apparent that the owners take great pride in making it nice. Everything was spotless! The surrounding grounds were also beautiful."
United States
Kathleen S.
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is NZ$500
includes taxes & fees
16 Dec - 17 Dec
Family Friendly Hilltop House In Putney Vermont
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

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 favorite 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 depends 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 NZ$438 per night. Entering your travel dates in the search wizard you might find 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?

Chester Farmhouse Ski Retreat near Slopes: This holiday home rental outside of Surry has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.