Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

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

Guest favorite

Apartment in Woodstock Valley

4.93 out of 5 average rating, 331 reviews

“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.

Sep 21 – 28

€ 180 per night
Guest favorite

Farm stay in Southbridge

4.98 out of 5 average rating, 162 reviews

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.

Aug 6 – 13

€ 194 per night
Guest favorite

Guest suite in Thompson

4.98 out of 5 average rating, 112 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

Aug 19 – 26

€ 156 per night

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

Guest suite in Brooklyn

4.92 out of 5 average rating, 152 reviews

Affordable In-Law Apartment in Brooklyn, CT

Nov 4 – 11

€ 78 per night
Superhost

Cottage in Chaplin

4.88 out of 5 average rating, 128 reviews

Clark Cottage in the historic village in Chaplin

Oct 23 – 30

€ 147 per night
Guest favorite

Home in Southbridge

4.94 out of 5 average rating, 302 reviews

Charming Cape--Kid & Dog Friendly 🐾

Apr 23 – 30

€ 222 per night
Guest favorite

Apartment in Stafford

4.88 out of 5 average rating, 140 reviews

Historic 1 bedroom suite

Dec 17 – 24

€ 97 per night
Guest favorite

Loft in Tolland

4.98 out of 5 average rating, 148 reviews

Cozy studio loft

Jan 8 – 15

€ 108 per night
Guest favorite

Cottage in Thompson

4.98 out of 5 average rating, 112 reviews

Private waterfront cottage on Quaddick Lake, CT

May 13 – 20

€ 264 per night
Guest favorite

Apartment in Woodstock

4.94 out of 5 average rating, 18 reviews

Woodstock Red Barn | Private Apt in Idyllic Town

Apr 16 – 23

€ 138 per night
Guest favorite

Farm stay in Woodstock

5.0 out of 5 average rating, 53 reviews

Quiet Cottage on a Working Goat Farm in Woodstock

Jul 10 – 17

€ 136 per night
Guest favorite

Apartment in Woodstock

4.98 out of 5 average rating, 66 reviews

Private apartment in a country home

Sep 15 – 22

€ 142 per night
Guest favorite

Home in Woodstock

4.93 out of 5 average rating, 15 reviews

Country Lake Oasis

Oct 20 – 27

€ 332 per night
Guest favorite

Bungalow in Pomfret

4.95 out of 5 average rating, 88 reviews

Pomfret private bungalow

May 30 – Jun 6

€ 156 per night
Guest favorite

Home in Ashford

4.87 out of 5 average rating, 31 reviews

Amazing lake home w/ amenities.

Feb 17 – 24

€ 134 per night

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

€ 46 before taxes and fees

Destinations to explore

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