Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

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Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 199 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

Jul 17 – 24

R2,533 ZAR per night

Guest favorite

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.

Aug 29 – Sep 5

R3,831 ZAR per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 429 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.

Jun 30 – Jul 7

R2,052 ZAR per night

Guest favorite

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.

Aug 26 – Sep 2

R2,698 ZAR per night

Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 223 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.

Mar 18 – 25

R2,778 ZAR per night

Guest favorite

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.

Dec 24 – 31

R1,793 ZAR per night

Guest favorite

Condo in Brattleboro

4.92 out of 5 average rating, 283 reviews

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

Jul 23 – 30

R1,749 ZAR per night

Guest favorite

Apartment in Brattleboro

4.95 out of 5 average rating, 150 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.

May 10 – 17

R2,279 ZAR per night

Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 479 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

Mar 16 – 23

R3,500 ZAR per night

Guest favorite

Apartment in Dummerston

4.96 out of 5 average rating, 160 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.

Sep 7 – 14

R1,696 ZAR per night

Guest favorite

Apartment in Brattleboro

4.96 out of 5 average rating, 284 reviews

Apt in town 2 BR/2 levels in Victorian Farmhouse

We're two blocks from Main Street and it's just a few blocks more to the local theater, art and culture, a variety of excellent restaurants, and walking trails. You’ll love my place because we're so close to town, but not on a main through street, so it's quiet here. My place is good for couples, or a group of friends, solo adventurers, traveling professionals, and for a great get-away.

May 1 – 8

R2,649 ZAR per night

Guest favorite

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.

May 29 – Jun 5

R2,348 ZAR per night