Holiday houses in Guilford

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Top-rated holiday rentals in Guilford

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Bernardston

4.88 out of 5 average rating, 285 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

12–19 Jan

$243 NZD per night

Guest favourite

Cottage in Guilford

4.97 out of 5 average rating, 105 reviews

Green River Cottage Retreat

Our 3 bedroom cottage is situated along the Green River on a quiet dirt road 20 minutes from Brattleboro. Bask in the beauty of rural Vermont—sit on the front deck and enjoy the sounds of the river and stargaze while surrounded by the enchanting beauty of the rolling hills. Right outside the door you can walk, bike or jog for miles alongside the picturesque Green River. Our cottage is the perfect place to relax or enjoy all the area has to offer. Perfect for couples, families, friends.

17–24 Sep

$363 NZD per night

Guest favourite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 427 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

6–13 Jul

$188 NZD per night

Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

2–9 Jan

$283 NZD per night

Guest favourite

Apartment in Marlboro

4.94 out of 5 average rating, 221 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly goats and dogs, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

22–29 Nov

$267 NZD per night

Guest favourite

Guest suite in Brattleboro

4.94 out of 5 average rating, 518 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

21–28 Dec

$184 NZD per night

Guest favourite

Apartment in Brattleboro

4.96 out of 5 average rating, 149 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

6–13 Jul

$230 NZD per night

Guest favourite

Cabin in Guilford

4.96 out of 5 average rating, 477 reviews

Serenity Now - Couples Retreat or Writer's Dream

COUPLES RETREAT or SOLO EXCURSION Perfect setting to swoon your partner or write the novel of your dreams. A romantic destination for Engagements, Honeymoons & Anniversaries. Guilford Vermont - no cleaning fee - Easy drive from Boston & NYC ROMANCE SPECIAL - Guests staying 3 nights or more, receive hard cider, cheese and chocolate ($50.00 value) Ask me about ELOPEMENT & VOW RENEWAL CEREMONIES

30 Aug – 6 Sep

$345 NZD per night

Guest favourite

Apartment in Dummerston

4.96 out of 5 average rating, 158 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

12–19 Sep

$175 NZD per night

Guest favourite

Apartment in Brattleboro

4.9 out of 5 average rating, 483 reviews

Cozy, Private & Great location for exploring VT !

The apartment is centrally located, cozy, quiet and private. It has been set up to be a comfortable retreat. It's private entrance leads upstairs to an open living room/ kitchen space. The back door opens to a deck overlooking a ball field and green hills. The sleeping nook contains a queen size , metal framed bed. The mattress is comfortable and the sheets are soft. VT charges 10% tax

21–28 Sep

$180 NZD per night

Guest favourite

Cottage in Guilford

4.92 out of 5 average rating, 131 reviews

Peaceful Cozy Cottage in the Vermont Woods

Charming one bedroom cottage nestled in the Green Mountains of Southern Vermont. With all the comforts of a country retreat, the cottage is perfect for couples and can accommodate up to three adults. Just over three hours by car from New York City, two hours from the Boston area. The cottage and natural surroundings offer a chance to relax and unwind in a private, peaceful setting.

4–11 Jun

$233 NZD per night

Superhost

Cabin in Brattleboro

4.89 out of 5 average rating, 441 reviews

Cottage

The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

28 May – 4 Jun

$251 NZD per night