
House holiday rentals in Londonderry
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Top-rated house rentals in Londonderry
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House rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

The 1770 House
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

SugarBear- Pool, AC, Sauna, Gym, Tennis!
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

Historic Home on 17 acres of land. Go escape!
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Weekly house rentals

Luxury VT Retreat. Breathtaking Views & Sunsets
First and foremost, Julia is one of the most accommodating and most responsive hosts I’ve ever had. She was very friendly and proactively looked for ways to help me and my group feel welcome. Beautiful space scenically located on a Vermont mountainside - would absolutely recommend!

Just an Incredible Vermont Mountain Retreat
My family and I enjoyed four days at the cabin, and it was exactly what we needed! Couldn't have been happier with our stay. We enjoyed the property's seclusion but also that it wasn't too far from several towns and ski resorts--truly a win-win. Would definitely come back.

Mountain View Getaway
My partner and I were craving a weekend getaway to unwind and escape our hectic schedules. Nicole’s place was the perfect fit! It was exactly as depicted in the listing - quiet, private, and with a breathtaking view of Mt Tabor. Manchester, VT, was just a short drive away, offering a delightful mix of shopping and dining options. This place exceeded our expectations and was exactly what we needed!

Vermont Mirror House
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

The Aster Chalet: a modern family retreat
This place was beautiful! We enjoyed all of the little touches including the thoughtful snack platter, the night lights around the house, sound machine, games, fireplace, and the comfy blankets. The mud room cubbies were so great for all of our ski gear. It really does look just like the photos. So modern and clean. Very pleased with our stay.

Hot Tub, Mtn View-Mins to Hiking, Biking &Swimming
We had a wonderful weekend. We hiked on Friday while we had beautiful weather, enjoyed grilling out & the hot tub. Saturday since the weather didn't cooperate we went for a drive & for lunch. Enjoyed the game room while having some local craft beers (we were fortunate enough to meet & taste beers from Twisted Horn, if they're open stop in). The house was spacious, we thoroughly enjoyed staying here.

Close to 4 mnts. Private stream! King bed. Dogs OK
Had a great time staying here with my family. Perfect location for skiing at Bromley very cozy and the owner was helpful and responsive.

Black Star Barn, Mountain Retreat w/ Hot Tub
We were 2 couples and had the perfect stay! Really cozy house with a great porch and hot tub! We loved playing ping pong as well! Would 100% stay there again!!
Private house rentals

Ludlow Lake & Ski Cottage - Adventure Awaits!
Exceptional experience! This is one of the relaxing place I have ever been! Large windows give you sense of experience living in nature. The stunning view gives you awesome feeling in any weather conditions.The house is nice, clean and equipped with pretty much everything. They have all the utensils for cooking and lots of toys for kids both indoor and outdoor. They also have paddles boat and kayak to use at anytime ! In addition, Brian is very respectful, responsible and quick to respond for any questions. All together Feel like you live in your own house. Great vacation spot without any doubt.

Lakeview | Family-friendly | Stargaze | Relax
Absolutely beautiful stay! The place was spotless, with an amazing lake view that made for a perfect, peaceful getaway. The beds were all very comfortable, and the amenities provided truly made it feel like being at home. There were plenty of towels, toilet paper, and paper towels, which was a thoughtful touch. Communication with the host was smooth, and check-in and check-out were super easy. A great spot to decompress and relax. I highly recommend!

Modern cabin close to all mountains
We had a wonderful, cozy stay here! This was a perfect place for our families and was a great space for our kids and dogs. Tom was highly responsive to our questions which is so appreciated! This home is about 25 mins from Okemo and even closer to Magic Mountain! There’s a great little grocery nearby too!

Lakefront gem
Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!

2-Bedroom Home, 7 Minutes From Stratton Mountain
Ariana’s place was great after a day of snowboarding at Stratton. Great location, the home was cozy and we had a great time relaxing at the house. Ariana was responsive to our question and the home was well equipped to enjoy a meal at home after being out all day.

Tallwood Pine Chalet
Perfect location for our winter getaway. Grocery store right around the corner and close to Magic Mtn and Wild Wings XC. Would stay here again

Snowy Holidays at the Octagon w/ 3 Fireplaces!
Bermet and Danny’s home was the perfect spot to host my husband’s surprise 40th birthday ski weekend with friends. Along the way, they were very responsive to our messages, flexible with our needs (early check-in, etc.) and friendly to deal with. The house was really unique and super convenient to several mountains. This was a 5-star stay and I would visit again for sure! Thanks to the hosts for their hospitality.

Londonderry Links
Great property for my family with lots to explore. The house is laid out very well and the beds are very comfortable!
Quick stats about house rentals in Londonderry
Total rentals
110 properties
Nightly prices starting at
$154 SGD before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Autumn Mountain Winery
- Lake George Expedition Park
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Bretwood Golf Course