House holiday rentals in Town of Rockingham

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Popular amenities for Town of Rockingham 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 stars2 weeks 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!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month 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 stars2 weeks 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!! 🤩

Weekly house rentals

Guest favourite
Home in Springfield
4.97 out of 5 average rating, 67 reviews

Charming New England Cape

SusanRating, 5 stars1 month ago
Really nice peaceful place to stay. Was super clean and a most interesting house with many antiques, brought back many memories from childhood. Host was very responsive and very friendly. Would definitely stay there again!
Guest favourite
Home in Newport
4.98 out of 5 average rating, 47 reviews

Lakeview | Family-friendly | Stargaze | Relax

LuzRating, 5 stars1 week ago
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!
Guest favourite
Home in Chester
4.88 out of 5 average rating, 41 reviews

Historic 150-Year-Old Farmhouse | Jacuzzi included

CarlyRating, 5 stars2 weeks ago
This was truly an oasis for me and my family during our stay in beautiful Vermont. Collin was an excellent host and was accommodating during my entire stay. It is a large beautiful farm house with the antique charm but updated amenities. My children enjoyed the hot tub and the large outdoor area while I had the space to cook some excellent meals. The town is just lovely with friendly people everywhere you go. I highly recommend Smitty’s for a local small grocery store. Our host Collin even gave us a gift card to a local pizza place that is superb. I will certainly stay again!
Top Guest favourite
Home in Springfield
5 out of 5 average rating, 26 reviews

Scandinavian Serenity Close to Okemo

ColleenRating, 5 stars1 week ago
We adore this perfectly peaceful getaway in VT! This was our third stay at the Scandanadian oasis and for anyone visiting VT, you have to see it in June! So many beautiful flowers in bloom decorating the property. Yulia and Mark were absolutely wonderful and responsive. The house is always immaculate! Highly recommended!
Guest favourite
Home in Bellows falls
4.9 out of 5 average rating, 10 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars4 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Top Guest favourite
Home in East Dover
5 out of 5 average rating, 50 reviews

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 stars1 week 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.
Guest favourite
Home in Chester
5 out of 5 average rating, 7 reviews

Chester Mountain View

JedRating, 5 stars4 months ago
Great house and location to bring family and friends for a ski trip getaway! Very responsive and attentive host. Had a wonderful stay.
Top Guest favourite
Home in Jamaica
5 out of 5 average rating, 9 reviews

Raven Wood Cottage

LeeannRating, 5 stars3 months ago
we had such a nice stay at the cabin and had everything we needed for our time away. Robert was quick to respond to questions and the house was really clean and comfortable. We loved the little touches too - the record player, local art, etc. and it was the best nights sleep I've had in months. one of my favorite air BNB experiences to date.

Private house rentals

Top Guest favourite
Home in Walpole
4.99 out of 5 average rating, 76 reviews

Charming, Large House in Walpole NH /VT. Border

DeniseRating, 5 stars1 week ago
Comfy beds, well equipped kitchen, plenty of room to spread out, lots of interesting things to look at in the house, beautiful gardens, close to Burdick’s (yum) and the list goes on!! It was the perfect place for my family while we attended a wedding in the area!!
Top Guest favourite
Home in Walpole
4.91 out of 5 average rating, 22 reviews

Country Cottage

CarolineRating, 5 stars2 weeks ago
This was the most comfortable place we have ever stayed at, and we truly felt at home. Everyone in our party commented on how it had everything they needed. Welcoming. Quaint. Warm. Comfortable. Convenient. Heart warming. This was absolutely a home away from home. A great host, terrific house, and a beautiful garden in a cute little town. We all totally recommend this location.
Top Guest favourite
Home in Bradford
5 out of 5 average rating, 52 reviews

Ski Sunapee or Pat’s Peak Look To The Mountain

MichaelRating, 5 stars3 weeks ago
Beautiful place with a mountain view like no other! Much needed peace and quiet.. Very affordable and Judith is a wonderful host. Very responsive to my messages. I will definitely be looking for availability next time I'm in town! Thanks for being so accommodating!
Top Guest favourite
Home in Windsor
4.99 out of 5 average rating, 95 reviews

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

AmandaRating, 5 stars1 week ago
We had a great stay! The house was well-appointed and comfortable. We especially loved the covered porch and beautiful view. It was a great home base for exploring the area, including several nearby hiking trails, Woodstock and Quechee (about a half hour away), and Brattleboro (less than an hour away). Ab was a fantastic host. He was proactive with communication and even checked in with us to make sure we had power after some strong thunderstorms that had moved through the area.
Top Guest favourite
Home in Chester
5 out of 5 average rating, 34 reviews

Cozy 1850 farmhouse in Stone Village of Chester

Kristopher (& Kay)Rating, 5 stars3 months ago
Truly a historic home and a very nice place to stay in the area. Exceptionally well supplied for preparing meals! A big plus for us as we don’t like to eat every meal out. Communicative hosts and pleasant environment, I recommend this location to folks visiting the area!
Guest favourite
Home in Guilford
4.92 out of 5 average rating, 50 reviews

Vermont Mirror House

GeorgeRating, 5 stars2 weeks 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 Chester
4.98 out of 5 average rating, 52 reviews

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain

RitaRating, 5 stars6 days ago
Nice and quiet out of the way place. Perfect for a quick getaway for a few days. We will definitely be going back.
Top Guest favourite
Home in Londonderry
4.96 out of 5 average rating, 24 reviews

The Green Mountain Chapel

SeanRating, 5 stars2 months ago
A good location just on the edge of town. it doesn't offer the remoteness of some place as you are on the main street. but that said it's perfect for small town adventures, which is what we wanted. Tyler was very responsive and helpful as far as local recommendations. We would absolutely stay there again.

Destinations to explore

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