Vacation rentals in Whitingham

5 out of 5 average rating, 10 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

VanessaRating, 5 stars1 month ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

4.85 out of 5 average rating, 13 reviews

Home in Hoosick Falls

Enjoy Fall & Experience Beautiful Changing Colors

AnthonyRating, 5 stars2 months ago

We stayed here for a few months while we looked for a home to buy after a work move. Over these months Delia and the home were great. The house provided everything we needed, was well kept, and everything we needed was provided for us while our things were in storage. Delia was communicative throughout and helped us when we needed to stay longer. A great property with great views and a great host.

4.86 out of 5 average rating, 125 reviews

Home in Readsboro

Beautiful Vermont! (Pet Friendly)

JudahRating, 5 stars4 months ago

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

4.96 out of 5 average rating, 25 reviews

Home in Old Chatham

Post and Beam Hilltop Sanctuary

CatherineRating, 5 stars3 months ago

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

4.91 out of 5 average rating, 98 reviews

Tiny home in Whitingham

Cozy Lakeside Tiny Home, Near Skiing

MelissaRating, 5 stars4 weeks ago

We had a lovely time at this tiny home. It was quiet and relaxing which is exactly what we were looking for. We enjoyed the hot tub and the sunny living room. It was cozy and cute. We took a few trips to Wilmington for food. It’s a cute town. We’d like to come back when the weather is better to enjoy some kayaking and hiking in the area.

4.91 out of 5 average rating, 134 reviews

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars3 weeks ago

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

5 out of 5 average rating, 4 reviews

Apartment in Glens Falls

Luxury Downtown Rental GF

AnthonyRating, 5 stars2 months ago

What a beautiful apartment. One of the nicest AirBnb's I have ever stayed at. Beautifully decorated and spacious. Everything was perfect. The location was perfect and parking was not an issue. Beautiful attention to detail. It even has an outdoor bbq and patio.

4.99 out of 5 average rating, 169 reviews

Home in Queensbury

Sunset Bay: Amazing waterfront w/ dock on 5 acres!

Florence GraceRating, 5 stars2 weeks ago

We stayed at Beth’s place in April. The place did not disappoint!! Beth thought of everything!! Our 20 yr old granddaughter stayed in the apartment. Absolutely great space. The view was stunning!! The place was extremely clean throughout. All the rooms are set up to relax and enjoy!! The basement was a wonderland for the kiddos. Every toy, game, and wide open space to play. It was a delightful stay.

5 out of 5 average rating, 26 reviews

Kiki's Mountain Chateau

DanielRating, 5 stars2 months ago

We highly recommend this house! Great space with everything we needed. The hot tub and fire place was a huge bonus. We had a 4W car and had no trouble driving through the back roads up to the house even during snow/sleet. Stephanie was fantastic- communicated well, helpful, accommodating and a pleasure to rent from.

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What guests are saying

2.5mi from the lake! Fire pit, arcade, yard games!

5 out of 5 average rating, 57 reviews3 weeks ago

Great spot! Stayed at Eric's place for a weekend with a group of college students (8) looking to hit the reset button and had plenty of space. It was spotless and comfortable, and we had no trouble finding what we needed. The virtual guide is also super helpful!

Home in Whitingham

What guests are saying

Amazing Views, Skiing Nearby and Amenities Galore!

5 out of 5 average rating, 8 reviews2 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!

Home in Bellows falls

What guests are saying

Tranquil Lake Cottage on 3 Acres with Large Deck

4.78 out of 5 average rating, 163 reviews1 week ago

We had a wonderful long weekend at Michelle’s place. We woke to 8 inches of snow in April, so made good use of the fireplace. We enjoyed exploring the area, found several fun places to ride our mountain bikes and showed our daughter another part of Massachusetts away from her college.

Cottage in Becket

What guests are saying

Sowilo Retreat All-Inclusive Maple House

4.98 out of 5 average rating, 47 reviews2 weeks ago

I had an absolutely wonderful stay! The place is incredibly clean and well-maintained, making it feel like a true home away from home. The host was amazing—so welcoming, kind, and attentive. They made me feel comfortable from the moment I arrived. One of the highlights of my stay was the delicious food they prepared. Every meal was cooked to perfection, and you can tell they put a lot of love and care into it. It truly elevated my experience! I highly recommend this place to anyone looking for a cozy and memorable stay. I would definitely love to come back again.

Tiny home in Cambridge

What guests are saying

Modern Chalet-private deck/firepit/ clubhouse pool

5 out of 5 average rating, 70 reviews2 months ago

Michelle and this property are absolute gems. The place is spotless, full of clean and well-maintained pots, pans, kitchen utensils, appliances, and tableware. All the rooms are well appointed and comfortable. We have learned from past rentals that the home is not always cleaned properly. So we normally wipe down all the counters, faucets and tables prior to use. This is the only home that we’ve rented that came away with ZERO dirt. Michelle’s very prompt communication contains very detailed information regarding the house and things to-do around the area. We are in awe of this house and Michelle. We hope that all future renters continue to respect the property so that many more can continue to enjoy it for years to come.

Cabin in Wilmington

What guests are saying

Lakefront cottage on burden lake in Averill park

4.89 out of 5 average rating, 9 reviews5 months ago

Very peaceful! Space was comfortable and it was nice to have a relaxing getaway and take a step back from work. Can’t wait to book again in the summer and take full advantage of what the lake has to offer! Lauren was an excellent host and very communicative.

Home in Averill Park

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Popular amenities for Whitingham vacation rentals

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Stay near Whitingham's top sights

The Ledges12 locals recommend

Spoonwood Cabin Creamery10 locals recommend

Honora Winery & Vineyard9 locals recommend

Honora Winery & Vineyard Tasting Room7 locals recommend

Remedy Wine Bar6 locals recommend

Jacksonville General Store Inc.5 locals recommend

Other great vacation rentals in Whitingham

5 out of 5 average rating, 14 reviews

Spring Hiking Pet Retreat I Game RM l ChimneyHill

LynnRating, 5 stars2 months ago

Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!

5 out of 5 average rating, 12 reviews

Condo in Dover

Cozy condo with direct mountain views and shuttle

RomanRating, 5 stars2 months ago

Elizabeth is a phenomenal host, the place is one of the best I ever stayed in.. super clean, well stocked, (especially the kitchen made great impression) very clean.. An excellent value for the money… big and accommodating…

4.93 out of 5 average rating, 14 reviews

Home in Monroe

The Camp

BrendaRating, 5 stars2 months ago

We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!

5 out of 5 average rating, 13 reviews

Home in Great Barrington

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago

We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!

4.86 out of 5 average rating, 35 reviews

Home in Manchester

Your VT Dream House: Fireplace, Pool, Dogs

AtulRating, 5 stars8 months ago

Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.

4.89 out of 5 average rating, 71 reviews

Home in Dover

Large Mount Snow Ski House with Hot Tub

AndyRating, 5 stars1 month ago

Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.

4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars1 week ago

Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.