House holiday rentals in Londonderry

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Popular amenities for Londonderry house rentals

House rentals with a pool

Guest favourite
Home in Killington
4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

KennethRating, 5 stars1 week ago
Very nice place easy access to routes 4 and 100 with plenty of things to do
Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars4 weeks ago
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!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
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.
Top Guest favourite
Home in Killington
4.99 out of 5 average rating, 135 reviews

SugarBear- Pool, AC, Sauna, Gym, Tennis!

JennRating, 5 stars1 month ago
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.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
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!! 🤩
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 218 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars3 months ago
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

Top Guest favourite
Home in Weston
5 out of 5 average rating, 10 reviews

Modern cabin close to all mountains

DevonRating, 5 stars3 months ago
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!
Top Guest favourite
Home in Jamaica
5 out of 5 average rating, 40 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

PaulinaRating, 5 stars3 months ago
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.
Superhost
Home in Londonderry
4.91 out of 5 average rating, 23 reviews

Tallwood Pine Chalet

EmilyRating, 5 stars4 months ago
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
Top Guest favourite
Home in Londonderry
5 out of 5 average rating, 21 reviews

Magical Retreat in Londonderry, 3 bd, EV charger

TsvetelinaRating, 5 stars3 months ago
Beautiful, spacious house, just as described. Clear instructions and responsive hosts.
Top Guest favourite
Home in East Dover
5 out of 5 average rating, 50 reviews

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 stars2 days ago
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.
Superhost
Home in Winhall
4.78 out of 5 average rating, 9 reviews

Stratton; 8 min! Swimming, 2 min. Pet friendly

AlisonRating, 5 stars10 months ago
Kelly was very responsive and helpful. She went out of her way to get us a last minute booking and it didn’t disappoint! It was clean, well stocked and very comfortable! I will definitely book this again when its available!!!
Guest favourite
Home in Londonderry
4.91 out of 5 average rating, 22 reviews

Londonderry Links

KaylaRating, 5 stars6 months ago
Great property for my family with lots to explore. The house is laid out very well and the beds are very comfortable!
Guest favourite
Home in Dorset
4.92 out of 5 average rating, 50 reviews

Mountain View Getaway

OliviaRating, 5 stars2 weeks ago
We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!

Private house rentals

Guest favourite
Home in Andover
5 out of 5 average rating, 6 reviews

River House w/ Hot Tub! Close to Mountain & More

JessicaRating, 5 stars4 months ago
This house was the best ski weekend away! Conveniently located yet secluded for a peaceful stay. The home itself is spacious, charmingly rustic, and thoughtfully stocked with everything we needed—especially the fully equipped kitchen, which made cooking a breeze. The atmosphere was cozy and inviting, making it the ideal spot to relax and unwind. Highly recommend.
Top Guest favourite
Home in Argyle
5 out of 5 average rating, 18 reviews

Lakefront gem

RebeccaRating, 5 stars1 month ago
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!
Guest favourite
Home in Ludlow
4.9 out of 5 average rating, 92 reviews

The Bluebird Day Chalet 2 bed dtwn Ludlow Village

BrianRating, 5 stars2 months ago
It is a great place. Convenient to downtown and a short ride to Okemo.
Guest favourite
Home in Andover
4.9 out of 5 average rating, 10 reviews

Vermont's BEST Spring time Log Cabin Retreat!

RachelRating, 5 stars3 months ago
We stayed for a long weekend and our stay with Sarah was perfect! The cabin is even cuter than the photos and is very cozy. It was perfect for our ski weekend at Okemo (only 20ish minute drive!). Very quiet and peaceful. The horses and the pupper on the property were extra charming. When we arrived, there was popcorn and candy to welcome us and helpful information for our stay. The cabin is warm and inviting and has everything you might need. Everything about the space is clearly very well maintained, including the horses which are obviously well cared for and loved. We definitely plan to stay here again!
Guest favourite
Home in Chester
4.91 out of 5 average rating, 90 reviews

Snowy Holidays at the Octagon w/ 3 Fireplaces!

KatieRating, 5 stars3 months ago
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.
Guest favourite
Home in Jamaica
4.73 out of 5 average rating, 11 reviews

Cozy Cottage at Cold Moon Farm!

VictoriaRating, 5 stars2 months ago
Very cozy cottage for a short ski trip. It was nice and clean, and it was in a very convenient location near Stratton.
Guest favourite
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars1 week ago
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.
Top Guest favourite
Home in Weston
5 out of 5 average rating, 28 reviews

Mountain View Retreat

LibbyRating, 5 stars2 weeks ago
We were looking to quickly book a place to get away after our painters' schedule changed and Andrew responded so quickly to help. We booked 10PM the night before and he was still able to get cleaners over next day so the place was ready for us. The property is really beautiful, you can see little pieces of the mountains between the trees and it's a really quiet and peaceful area. Our dogs loved the fenced in yard. Far enough away to feel remote but close enough where you can get to a nice dinner within 20 minutes. Would highly recommend.

Quick stats about house rentals in Londonderry

  • Total rentals

    110 properties

  • Nightly prices starting at

    $184 AUD 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Londonderry
  6. House rentals