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Vacation rentals in Guilford

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Top-rated vacation rentals in Guilford

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

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Guest suite in Greenfield

4.94 out of 5 average rating, 178 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Guesthouse in Brattleboro

4.98 out of 5 average rating, 219 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.

Rental unit in Dummerston

4.96 out of 5 average rating, 195 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. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Cottage in Guilford

4.96 out of 5 average rating, 118 reviews

Green River Cottage

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.

Guesthouse in Brattleboro

4.92 out of 5 average rating, 489 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.

Camper/RV in Guilford

4.93 out of 5 average rating, 107 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Barn in Marlboro

4.95 out of 5 average rating, 294 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.

Guest suite in Brattleboro

4.94 out of 5 average rating, 555 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.

Condo in Brattleboro

4.93 out of 5 average rating, 325 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 .

Cabin in Guilford

4.96 out of 5 average rating, 511 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

Guest suite in Guilford

4.97 out of 5 average rating, 126 reviews

Private, Quiet Studio With Mountain Views

Formerly a musician's studio, the studio apartment overlooks an open field with 100 mile views of the distant mountains. Well insulated for sound and comfort, the studio offers privacy, peace and quiet and a chance to relax and unwind, away from the demands of everyday life. Functionally and decoratively furnished, the details are simple and a bit homespun. Original artworks complete the decor.

Guesthouse in Putney

4.97 out of 5 average rating, 270 reviews

Cozy cottage loft and retreat

Returning guests, please ask about our discount! Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

Vacation rentals for every style

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Hotels

Stylish accommodations and amenities

Unique stays

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Homes

Comfortable places with all the essentials

Popular amenities for Guilford vacation rentals

Free parking on premises

Air conditioning

Stay near Guilford's top sights

Vermont Jazz Center14 locals recommend

Guilford Country Store7 locals recommend

Blueberry Haus7 locals recommend

Deer Ridge Farm - Cut flowers, maple syrup, berries, and local honey.4 locals recommend

Bonnyvale Environmental Education Center4 locals recommend

Sweet Pond State Park Parking Lot and Trailhead3 locals recommend

Other great vacation rentals in Guilford

Rental unit in Winchester

4.91 out of 5 average rating, 191 reviews

Downtown Loft next to Distillery

Rental unit in Shelburne Falls

4.95 out of 5 average rating, 195 reviews

Soaring 2-level loft w/ views in heart of downtown

Rental unit in Brattleboro

4.9 out of 5 average rating, 351 reviews

Quiet St in Town, gardens, terrace

Guest suite in Wilmington

4.92 out of 5 average rating, 752 reviews

Architectural GuestSuite

Tiny home in Wilmington

4.99 out of 5 average rating, 217 reviews

Beautiful Timber Frame Retreat

Guesthouse in Marlboro

4.97 out of 5 average rating, 157 reviews

Refined, serene and like no other, Marlboro, VT.

Tiny home in Orange

4.92 out of 5 average rating, 346 reviews

The Writer's Retreat: A Sweetwater Stay

Rental unit in Newfane

4.97 out of 5 average rating, 433 reviews

Rock River Retreat: VT Oasis Pet Friendly

Quick stats about vacation rentals in Guilford

Total rentals
30 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

Are there family-friendly vacation rentals in Guilford?
Guilford has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Guilford have wifi?
Absolutely! We offer over 10 house rentals with wifi in Guilford. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Guilford have free parking?
Absolutely! We offer over 10 house rentals with free parking in Guilford. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Guilford have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Guilford. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Guilford?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Guilford?
Yes! Work meets play with ease at over 20 vacation rentals in Guilford featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore