Guesthouse holiday rentals in Addison County

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Top-rated Guesthouses in Addison County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Waitsfield

5.0 out of 5 average rating, 44 reviews

Beautiful Newly Constructed- 1 Bedroom Apartment

NEW CONSTRUCTION! Located just a 1/2 mile from the base of Mt. Ellen, access to classic Mad River Valley mountain bike trails just outside the door. This newly constructed apartment has over 1000ft of living space and large windows covering every wall. This quiet apartment is a great Vermont get away for a couple or small family. Spacious living room, kitchen, bedroom, combined with the natural light and views on two sides allows you to take in all the best that this part of Vermont has to offer

7–14 May

$685 NZD per night

Guest favourite

Guesthouse in Warren

4.97 out of 5 average rating, 31 reviews

Prickly Mtn. guest house - funky cool place

Get away from it all! Super cool renovated guest house that can either be rented along with the bigger main house, [4 story 3BR 2BA in Warren] as extra space, or as a separate rental. Quiet respite or romantic getaway. Cozy Elm wood stove right off the kitchen, & a new heat/air pump upstairs. This place has one bedroom which looks out onto an expansive deck with a private forest. Pull-out single bed in upstairs study for an extra guest.Washer/dryer, brand new fixtures & a sweet new bathroom.

13–20 Apr

$449 NZD per night

Guest favourite

Guesthouse in Warren

5.0 out of 5 average rating, 50 reviews

Detached Guest House Apt on 100 Secluded Acres

As a family vacation home since 1978, we finally moved to Warren full time in 2015 and built this guest house / detached garage apartment so family & friends could stay too. The home, off a paved road, is situated on 100 acres in a wooded meadow adjacent to the Green Mountain National Forest. While totally secluded, we are mere minutes to town, ski resorts, swim holes, hiking, biking, golf and the great area restaurants. If you are looking to make the move too, I am a licensed Vermont Realtor.

22–29 Oct

$470 NZD per night

Guest favourite

Guesthouse in Monkton

4.99 out of 5 average rating, 448 reviews

Cozy & Peaceful 40 Acre Retreat - Pups Welcome

The Barn at Grousewood, located 35 minutes to Burlington. If you are looking for a cozy, relaxing get away, we welcome you to our converted barn. Spin some vinyl, read or play games. Centrally located for day trips to breweries, hikes and restaurants. We have hiking trails for snowshoeing and exploring our woods full of wildlife. Deer, bear, bobcat, owls, porcupine, wild turkey, grouse and more. Enjoy a fire outside or relax in front of the hearth. WiFi for traveling workers & dog friendly.

23–30 Jun

$331 NZD per night

Guest favourite

Guesthouse in Bristol

5.0 out of 5 average rating, 31 reviews

Studio Retreat

About this Space Our cozy Studio Retreat is nestled in the woods on the 2nd floor of our detached garage, 5 min outside the charming village of Bristol. Bristol has several very good restaurants, shops, an art gallery and a library. You'll find hiking, biking trails and swimming. Middlebury is 15 min away and offers art galleries, breweries, a winery, shops, restaurants, hiking, skiing and more. Burlington is 45 min away, Sugarbush & Mad River Glen ski areas are just 30 min away. Lots to do!

30 Aug – 6 Sep

$309 NZD per night

Guest favourite

Guesthouse in Middlebury

4.85 out of 5 average rating, 48 reviews

Private Downtown Middlebury Home Walk Everywhere

Enjoy the beauty of Vermont in a convenient downtown spot. This well-appointed, private two bedroom home is in a prime location. Hardwood floors throughout. Dining Room. Full kitchen. Small deck. Walk to the Coop, Royal Oak coffee, and Middlebury College. This is the perfect stay for graduation, parent's weekend, skiing, or summer getaway in Vermont. Owner lives next door and is able to provide suggestions for great food or local arts events. Great for small families. Strictly No Pets.

6–13 May

$273 NZD per night

Guest favourite

Guesthouse in Monkton

4.98 out of 5 average rating, 105 reviews

Beautiful, 1 BR guesthouse

Lovely, light filled guest house built in 2019. Situated on 12 acre property with lovely views, starry night sky, great biking, hiking and x-country skiing from the cottage. Adjacent to Raven Ridge Natural Area with short hike offering beautiful views of the valley and Lake Champlain. Hinesburg, Bristol and Vergennes are 10-20 minutes, 30 minutes to Burlington and Middlebury. 2 hours to Montreal. Please don’t try booking for the April 2024 eclipse - I have family coming!

12–19 Nov

$274 NZD per night

Guest favourite

Guesthouse in Middlebury

4.85 out of 5 average rating, 79 reviews

Historic Farmhouse in Middlebury

We offer a historic, four bedroom farmhouse in a peaceful, rural Vermont setting surrounded by wetlands, forrest, and farms. This is a family and pet friendly property with a private entrance, full kitchen, living and dining areas, full and half bathrooms, access to our fenced backyard, and dedicated laundry facilities. By making arrangements ahead of your stay, you can use our 3 season party barn; send us a message letting us know how and when you would like to use it.

3–10 Aug

$456 NZD per night

Guest favourite

Guesthouse in Vergennes

4.98 out of 5 average rating, 91 reviews

Private Guesthouse in the heart of Vergennes

Completed in 2013, the Guesthouse perfectly complements the 1871 Victorian home to which it is attached. Located on Main Street in historic Vergennes, Vermont, our home is one of several fine examples of the architecture of the 19th Century that grace our City. Our thriving downtown is a short walk away, boasting exceptional dining and shopping opportunities. Vergennes is a 20-minute drive away from Middlebury College, and 45 minutes from Burlington.

14–21 Apr

$392 NZD per night

Guest favourite

Guesthouse in Salisbury

4.96 out of 5 average rating, 23 reviews

Stylish & Welcoming *All April dates $99/night*

Come swim, hike, or ski while staying at our welcoming and comfortable 2nd floor studio apartment with plush linens, comfortable King bed, a well equipped kitchenette plus space to relax, work & play. + Garage parking. 7 min from Middlebury with all its amenities 5 min from Lake Dunmore 13 min from Brandon 16 min from Rikert Outdoor Center for cross country 18 min from Snowbowl for down hill skiing 32 miles - approx 50 mins from Killington

27 Aug – 3 Sep

$416 NZD per night

Guest favourite

Guesthouse in Salisbury

4.93 out of 5 average rating, 83 reviews

Miss Dee's Retreat

A natural light-filled garage apartment in a serene wooded setting awaits you after a day of adventures. Fall asleep to woodland sounds of crickets & peeper frogs on a super-comfy queen-sized bed with Casper Wave mattress & soft linens. Awaken to the sound of birdsong & start your day with a cup of coffee or tea on the patio. Power up for another day of adventuring with a breakfast of eggs from our happy hens.

2–9 May

$244 NZD per night

Guest favourite

Guesthouse in Panton

4.98 out of 5 average rating, 55 reviews

Serene cottage retreat near Vergennes & Middlebury

Welcome to the cottage at Calendar Fields, a private guesthouse & farm pool overlooking pastoral fields, a pond and the backdrop of the Adirondacks. The cottage is filled with natural light, cozy furniture, textiles, local art and vintage accents. Our location offers a rural retreat with close access to quintessential Vermont hamlets Vergennes (10min), Bristol (25min) & Middlebury (25min).

11–18 Sep

$301 NZD per night