Vacation rentals in Woodstock

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodstock

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

Guest favorite
Apartment in Woodstock Valley
“Tranquillity on the Lake ” Woodstock Valley, Ct.
Spring and Summer are upon us. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. Featuring Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen -stove, full refrigerator, microwave. Enjoy private deck, propane fire pit, gaze at the moon & stars. Cook-Propane grill. Enjoy scenic walks around the lakes. Wake up to amazing sunrises. RELAX, ENJOY TRANQUILITY every season. New addition Woodstock Valley Country within two miles.
Nov 19 – 26
ﺩ.ﺇ484 per night
4.93 out of 5 average rating, 330 reviews
Guest favorite
Treehouse in Thompson
The Tree House at Underhill Hollow
The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.
Mar 25 – Apr 1
ﺩ.ﺇ390 per night
4.96 out of 5 average rating, 327 reviews
Guest favorite
Farm stay in Southbridge
High Grass Farm
Get cozy in front of the fireplace and enjoy a romantic getaway in our beautiful and historic old house. One of the top 16 farm stays in New England! Our 1780's farmhouse has been completely renovated and retains its rustic country feel. Experience early American period life with only a few modern conveniences (e.g. full laundry and 5G wi-fi). Our secluded setting on 19 acres in southern Mass is minutes from I-90 and I-84, and borders CT, Old Sturbridge Village and the Westville recreation area.
Nov 30 – Dec 7
ﺩ.ﺇ570 per night
4.98 out of 5 average rating, 161 reviews

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Roseland Cottage18 locals recommend
Woodstock Fair5 locals recommend
Sweet Evalina's Stand9 locals recommend
Roseland Park5 locals recommend
Mansion At Bald Hill7 locals recommend
Woodstock Orchard7 locals recommend

Other great vacation rentals in Woodstock

Guest favorite
Apartment in Stafford
Historic 1 bedroom suite
Jul 26 – Aug 2
ﺩ.ﺇ278 per night
4.88 out of 5 average rating, 137 reviews
Guest favorite
Home in Southbridge
Charming Cape--Kid & Dog Friendly 🐾
Sep 8 – 15
ﺩ.ﺇ678 per night
4.94 out of 5 average rating, 302 reviews
Superhost
Cottage in Scituate
5 Star cottage in historical Clayville
Apr 3 – 10
ﺩ.ﺇ313 per night
4.9 out of 5 average rating, 192 reviews
Guest favorite
Loft in Tolland
Cozy studio loft
Sep 6 – 13
ﺩ.ﺇ309 per night
4.98 out of 5 average rating, 145 reviews
Guest favorite
Cabin in Webster
The Camp
Sep 10 – 17
ﺩ.ﺇ456 per night
4.92 out of 5 average rating, 144 reviews
Guest favorite
Farm stay in Woodstock
Quiet Cottage on a Working Goat Farm in Woodstock
Nov 2 – 9
ﺩ.ﺇ371 per night
5.0 out of 5 average rating, 53 reviews
Guest favorite
Apartment in Woodstock
Private apartment in a country home
Mar 19 – 26
ﺩ.ﺇ416 per night
4.98 out of 5 average rating, 66 reviews
Guest favorite
Apartment in Woodstock
Woodstock Red Barn | Private Apt in Idyllic Town
May 28 – Jun 4
ﺩ.ﺇ422 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Woodstock
Country Lake Oasis
Oct 30 – Nov 6
ﺩ.ﺇ918 per night
4.93 out of 5 average rating, 15 reviews
Guest favorite
Bungalow in Pomfret
Pomfret private bungalow
Oct 19 – 26
ﺩ.ﺇ479 per night
4.95 out of 5 average rating, 88 reviews
Guest favorite
Home in Ashford
Amazing lake home w/ amenities.
Jan 23 – 30
ﺩ.ﺇ422 per night
4.9 out of 5 average rating, 30 reviews
Guest favorite
Home in Woodstock
Secluded 2 Acre Lake Front Home!
Dec 27 – Jan 3
ﺩ.ﺇ1,396 per night
4.84 out of 5 average rating, 86 reviews

Quick stats about vacation rentals in Woodstock

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.2K reviews

Nightly prices starting at

ﺩ.ﺇ184 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Windham County
  5. Woodstock