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House vacation rentals in Windham County

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Top-rated house rentals in Windham County

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

Guest favorite
Home in Sturbridge
Lake Front Home Sleeps 6-8 on a private Peninsula!
DIRECT WATER FRONT RENTAL! This breathtaking property is located on it's own PENINSULA! Stunning water views from almost every window. This updated year round charming family home features 3 BR, 2 bath, large living room w/sliders to a wrap around deck, incredible views from a huge, heated sun porch. The large yard with a dock, NEW Patio/Firepit, small private beach area, with kayaks, canoe and a row boat! SUMMER MONTHS: 5 Night minimum Thanksgiving andChristmas Holidays have a 3 night minimum
Oct 26 – Nov 2
$343 per night
Guest favorite
Home in Preston
New Lake Front Home w/ Game Room & Stunning Views
Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.
Feb 7 – 14
$350 per night
Guest favorite
Home in Woodstock
Cedar Ridge
In Connecticut's "Quiet Corner", a fully renovated 2-level house bathed in sunlight, with lovely flower beds and stunning hilltop views. Relax on its patios and in its small swimming pool, stroll along its forest paths, observe birds (including birds of prey) and other wildlife. New England's "Last Green Valley National Heritage Corridor" offers multiple attractions and is home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities.
Dec 20 – 27
$243 per night

Popular amenities for Windham County house rentals

House rentals with a pool

Guest favorite
Home in Sturbridge
Sturbridge MA 3 BR 2 1/2 Bath Home on Cedar Lake
Aug 4 – 11
$305 per night
Guest favorite
Home in Montville
Casino Wine Down House***
Jul 16 – 23
$544 per night
Guest favorite
Home in Stonington
Perfect New England Getaway has a pool/ hot tub
Oct 30 – Nov 6
$457 per night
Superhost
Home in Exeter
Nature's Nook
Sep 23 – 30
$277 per night
Guest favorite
Home in Norwich
Grand 9 BR Near Casinos
Feb 21 – 28
$607 per night
Guest favorite
Home in Hopkinton
Hopkinton Mass 3+ Bedrooms - Great location!
May 15 – 22
$136 per night
Guest favorite
Home in Griswold
Secluded Lakefront 10 Acre Estate Close To Casinos
Sep 18 – 25
$840 per night
Guest favorite
Home in Norwich
Private Villa 1 mi from Casino! Plus spa amenities
Dec 10 – 17
$121 per night
Guest favorite
Home in Coventry
Peaceful & Exquisite LAKE FRONT Property w/Pool
Oct 23 – 30
$875 per night
Guest favorite
Home in Norwich
Cozy Condo in Norwich- Minutes from Mohegan Sun
Dec 8 – 15
$135 per night
Superhost
Home in Mansfield
Mid-Century Modern Retreat
Jul 27 – Aug 3
$339 per night
Guest favorite
Home in East Haddam
5 Bedroom Country Home w. Private Pool!
Nov 12 – 19
$514 per night

Weekly house rentals

Guest favorite
Home in Lyme
“The Answer” Tidal River-Kayaks Fire pit Fireplace
Apr 19 – 26
$249 per night
Guest favorite
Home in Sturbridge
LAKE Retreat! Lakefront Home with Amazing Views!
Apr 9 – 16
$399 per night
Guest favorite
Home in Sturbridge
Modern Lakeview House -Chef's Kitchen, Strong Wifi
Sep 23 – 30
$182 per night
Guest favorite
Home in Southbridge
Charming Cape--Kid & Dog Friendly 🐾
Oct 20 – 27
$185 per night
Guest favorite
Home in Leicester
Cozy Lake House
Oct 28 – Nov 4
$201 per night
Guest favorite
Home in North Stonington
The Perch
Nov 15 – 22
$334 per night
Guest favorite
Home in Smithfield
Luxury Home | Fire Pit | Beach | Grill | 2 Decks
Mar 4 – 11
$349 per night
Guest favorite
Home in Coventry
Cozy Cottage * Coventry Lake* 15 min to UConn *
Jun 14 – 21
$162 per night
Superhost
Home in Union
Antique Home w Private Pond, Sturbridge /Brimfield
Aug 4 – 11
$178 per night
Guest favorite
Home in Auburn
Nice Remodeled Home In Auburn
Aug 5 – 12
$262 per night
Guest favorite
Home in Charlestown
Spacious RI Beach Escape
Mar 18 – 25
$91 per night
Guest favorite
Home in Brimfield
Brimfield Lakeside Home Away from Home
Jan 16 – 23
$195 per night

Private house rentals

Guest favorite
Home in Webster
Webster Waterfront Cottage Nestled in the Pines
Apr 29 – May 6
$350 per night
Guest favorite
Home in Killingly
"A FOOLS FOLLY FARM"a fun contemporary farmhouse
Feb 17 – 24
$140 per night
Guest favorite
Home in Killingly
3 bedroom cottage on Beautiful Alexander's Lake
Mar 9 – 16
$371 per night
Guest favorite
Home in Coventry
painted acres country getaway
Mar 26 – Apr 2
$185 per night
Guest favorite
Home in Union
The wabi-sabi lake house
Aug 10 – 17
$341 per night
Guest favorite
Home in Thompson
Waterfront Cottage on Quaddick Lake, Thompson CT
Sep 23 – 30
$213 per night
Guest favorite
Home in Eastford
Small town charm in Eastford
Nov 22 – 29
$180 per night
Guest favorite
Home in Ashford
Amazing lake home w/ amenities.
Jul 7 – 14
$235 per night
Superhost
Home in Holland
Holland MA - Pet friendly Lake Home!
Mar 21 – 28
$165 per night
Guest favorite
Home in Woodstock
Country Lake Oasis
Jun 1 – 8
$250 per night
Guest favorite
Home in Coventry
Cozy cottage 5 minutes from UConn
Jul 16 – 23
$347 per night
Guest favorite
Home in Stafford
Serene Lakefront Retreat
Jan 2 – 9
$126 per night

Destinations to explore