Search Your Destination Now!

Windham Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 37 Rentals

  • Charming Year Round Lakefront Cottage
    From $492 per night (USD)

    VRBO

    Charming Year Round Lakefront Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Our log cottage sits on a 15' high Point over-looking beautiful Alexander Lake affording 180 degree PANORAMIC WATER VIEW ...

    From $492 per night (USD)

    VRBO

    Details
  • Little House in the Big Woods- Tennis Court
    From $308 per night (USD)

    VRBO

    Little House in the Big Woods- Tennis Court

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Imagine staying in a house in Colonial Williamsburg, or OldSturbridge Village. The Little House at Jericho is an early ...

    From $308 per night (USD)

    VRBO

    Details
  • Charming Lakefront Cottage
    From $219 per night (USD)

    VRBO

    Charming Lakefront Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy, charming lakefront cottage on quiet, spring-fed Lake Chaffee. Relax on the deck, dock or private beach. Swim, c ...

    From $219 per night (USD)

    VRBO

    Details
  • Hampton 'Quiet Corner Cottage' w/ Fireplace & Yard
    From $343 per night (USD)

    Expedia

    Hampton 'Quiet Corner Cottage' w/ Fireplace & Yard

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    In the countryside of Connecticut, this charming cottage awaits anyone seeking an outdoor escape! Only 2 miles from Jame ...

    From $343 per night (USD)

    Expedia

    Details
  • Beautiful lake front home. Amazing view!
    From $411 per night (USD)

    VRBO

    Beautiful lake front home. Amazing view!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful lake front house. Right on the water! Large deck with amazing view of the lake. Fishing, swimming, boating, an ...

    From $411 per night (USD)

    VRBO

    Details
  • Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'
    From $702 per night (USD)

    Expedia

    Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Hardwood floors located throughout the first floor with 2 bedrooms and 1 full bath. The master bedroom has a queen bed w ...

    From $702 per night (USD)

    Expedia

    Details
  • Secluded 2-Acre Lakefront Home! Book Your Getaway!
    From $772 per night (USD)

    VRBO

    Secluded 2-Acre Lakefront Home! Book Your Getaway!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Escape to a Tranquil Lakefront Retreat in CT's "Quiet Corner"! Nestled on 2 private acres along the serene Lake Chamber ...

    From $772 per night (USD)

    VRBO

    Details
  • Rustic Farmette Studio with Hot Tub & Pool
    From $275 per night (USD)

    Expedia

    Rustic Farmette Studio with Hot Tub & Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Take it easy at this unique and tranquil getaway on 20 acres in CT’s Quiet Corner. Just an hour away from Boston, Provid ...

    From $275 per night (USD)

    Expedia

    Details
  • A fun filled,family friendly, farmhouse home, rural,but close to all amenities
    From $548 per night (USD)

    VRBO

    A fun filled,family friendly, farmhouse home, rural,but close to all amenities

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Located on four private acres of open land and surrounded by open fields and trees the property also features two horse ...

    From $548 per night (USD)

    VRBO

    Details
  • Magical Waterfront Cottage! Pet friendly!
    From $417 per night (USD)

    VRBO

    Magical Waterfront Cottage! Pet friendly!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Are you looking for a relaxing waterfront get away? This may be your place! This newly renovated cottage is located on a ...

    From $417 per night (USD)

    VRBO

    Details
  • Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
    From $391 per night (USD)

    VRBO

    Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: The Hidden Gem of Connecticut: Experience Lakefront bliss at our charming cabin boasting breathtaking water vi ...

    From $391 per night (USD)

    VRBO

    Details
  • Killingly Barnyard Studio in Wine Country!
    From $223 per night (USD)

    Expedia

    Killingly Barnyard Studio in Wine Country!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Make your way to Northern Connecticut and take in the stunning scenery surrounding this Killingly vacation rental! Feel ...

    From $223 per night (USD)

    Expedia

    Details
  • Serene 4-acre estate on private lake with hot tub
    From $926 per night (USD)

    VRBO

    Serene 4-acre estate on private lake with hot tub

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    In CT's tranquil and majestic "Quiet Corner" this private 4-acre estate located on Lake Chamberlain comes replete with y ...

    From $926 per night (USD)

    VRBO

    Details
  • Cozy Rural Guest House: Close to Wedding Venues
    From $278 per night (USD)

    Expedia

    Cozy Rural Guest House: Close to Wedding Venues

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Leave the day-to-day grind behind for a relaxing escape to this rural 1-bed, 1-bath vacation rental! ‘The Bear's Den’ is ...

    From $278 per night (USD)

    Expedia

    Details
  • Amazing lake house with everything you need!
    From $203 per night (USD)

    VRBO

    Amazing lake house with everything you need!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Full lake house with everything you may need. Lake access steps away from property. Kayaks fire pit. New kitchen and bat ...

    From $203 per night (USD)

    VRBO

    Details
  • Peaceful \Country Lake Oasis\ with private beach directly on site!
    From $548 per night (USD)

    VRBO

    Peaceful \"Country Lake Oasis\" with private beach directly on site!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Relax at our peaceful lakefront home with a private sandy beach, dock, kayaks, fire pit, deck seating, and beautiful wat ...

    From $548 per night (USD)

    VRBO

    Details
  • Stunning Lakefront Escape! Book Your Dream Getaway!
    From $740 per night (USD)

    VRBO

    Stunning Lakefront Escape! Book Your Dream Getaway!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in the idyllic setting along the shores of Lake Quasset, in Woodstock, CT, this property not only provides direc ...

    From $740 per night (USD)

    VRBO

    Details
  • SteamPunk Bunk House and Intergalactic Way Station
    From $188 per night (USD)

    Expedia

    SteamPunk Bunk House and Intergalactic Way Station

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    A farm stay like no other! The future is the past and the past is the future with STEAMPUNK details that delight at ever ...

    From $188 per night (USD)

    Expedia

    Details
  • Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
    From $327 per night (USD)

    VRBO

    Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: The Lake House, a two-story Designer's Dream, boasts scenic water and starry sky views. ● 397 Mbps Wi-Fi | ...

    From $327 per night (USD)

    VRBO

    Details
  • Quintessential New England Home w/ Patio & Grill!
    From $629 per night (USD)

    Expedia

    Quintessential New England Home w/ Patio & Grill!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Nestled in the heart of Putnam, 'Osmington Manor,' a 5-bedroom, 2-bath vacation rental, awaits your arrival. With a rich ...

    From $629 per night (USD)

    Expedia

    Details
  • Luxurious 5-BR home in peaceful 3+-acre setting with heated, salt-water pool!
    From $1267 per night (USD)

    VRBO

    Luxurious 5-BR home in peaceful 3+-acre setting with heated, salt-water pool!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Pristine and luxurious with inviting, cozy spaces inside and outside. This beautiful home is privately situated on over ...

    From $1267 per night (USD)

    VRBO

    Details
  • Mohegan Sun Getaway Large Group Retreat
    From $583 per night (USD)

    Expedia

    Mohegan Sun Getaway Large Group Retreat

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    10

    ✨ Welcome to Your Luxury Retreat Near Mohegan Sun ✨ Unwind in this beautifully designed 4-bedroom, 2-bath home where mod ...

    From $583 per night (USD)

    Expedia

    Details
  • Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
    From $257 per night (USD)

    VRBO

    Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Friends and family will be close to everything when you stay at this centrally located 2-bedroom apartment. Perfect spac ...

    From $257 per night (USD)

    VRBO

    Details
  • 4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
    From $528 per night (USD)

    VRBO

    4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Thread City Escape - a beautifully updated 4-bedroom, 2-bath home in the heart of Willimantic, Connecticut. T ...

    From $528 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi
    From $216 per night (USD)

    VRBO

    Charming 2-bedroom cottage on 7 acres of woods in Putnam with AC, WiFi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Private rustic cottage on 7 acres of woods. This 2-bedroom cottage at the end of a long driveway offers privacy and tran ...

    From $216 per night (USD)

    VRBO

    Details
  • Charming 2-bedroom country village house with AC in East Woodstock
    From $330 per night (USD)

    VRBO

    Charming 2-bedroom country village house with AC in East Woodstock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Nestled a few short blocks from East Woodstock Village, complete with cemetery, church (you can hear he bells from the ...

    From $330 per night (USD)

    VRBO

    Details
  • Spacious, unique barn with beautiful views.
    From $266 per night (USD)

    VRBO

    Spacious, unique barn with beautiful views.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our fi ...

    From $266 per night (USD)

    VRBO

    Details
  • Terrific 4-bedroom house with AC in Ashford
    From $420 per night (USD)

    Expedia

    Terrific 4-bedroom house with AC in Ashford

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Your Ashford adventure begins at this 4-bedroom house. Each room features a cozy queen bed, ensuring a wonderful night's ...

    From $420 per night (USD)

    Expedia

    Details
  • The Farmhouse at Golden Hill Farm
    From $1286 per night (USD)

    VRBO

    The Farmhouse at Golden Hill Farm

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The main house at Golden Hill Farm is a renovated farmhouse appointed with luxurious furnishings and amenities. Surround ...

    From $1286 per night (USD)

    VRBO

    Details
  • The McClellan Mansion
    From $705 per night (USD)

    Expedia

    The McClellan Mansion

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Resting on a sprawling estate in picturesque Woodstock, CT, this fully restored historic home blends timeless architectu ...

    From $705 per night (USD)

    Expedia

    Details
  • Direct Lakefront Retreat | Indian Ranch | Casinos
    From $536 per night (USD)

    VRBO

    Direct Lakefront Retreat | Indian Ranch | Casinos

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Luxury Lakefront Escape Create unforgettable memories at this beautiful lakefront retreat — the perfect destination for ...

    From $536 per night (USD)

    VRBO

    Details
  • Historic Greek Revival ‘Gathering House
    From $477 per night (USD)

    VRBO

    Historic Greek Revival ‘Gathering House

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to a one-of-a-kind experience! Once the South Killingly Congregational Church, this authentic Greek Revival land ...

    From $477 per night (USD)

    VRBO

    Details
  • Waterfront Tiny House Cabin Off Grid Camp in Historic Woodstock CT
    From $148 per night (USD)

    VRBO

    Waterfront Tiny House Cabin Off Grid Camp in Historic Woodstock CT

    Bedrooms:
    0
    Bathrooms:
    1
    Sleeps:
    4

    Located in Woodstock, CT this cabin sits on the shores of Chamberlain Pond, a popular fishing spot. This two acre proper ...

    From $148 per night (USD)

    VRBO

    Details
  • Half a mansion with three bedrooms and 3 1/2 Bathrooms!!
    From $232 per night (USD)

    Expedia

    Half a mansion with three bedrooms and 3 1/2 Bathrooms!!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    3

    Half a Mansion with three bedrooms and 3 1/2 Bathrooms with everything state-of-the-art. Superfast Wi-Fi, Egyptian cotto ...

    From $232 per night (USD)

    Expedia

    Details
  • MidCentury Modern Lakehouse: kayaks,firepit,steamshower, gourmt kitchn,fireplace
    From $702 per night (USD)

    VRBO

    MidCentury Modern Lakehouse: kayaks,firepit,steamshower, gourmt kitchn,fireplace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Escape to our tranquil lakeside Scandinavian mid-century modern retreat.A 3-bedroom house in the quiet corner’s Woodstoc ...

    From $702 per night (USD)

    VRBO

    Details
  • 400 Sq Ft of Paradise in a Forest
    From $538 per night (USD)

    Expedia

    400 Sq Ft of Paradise in a Forest

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    14

    Escape to Your Private New England Colonial Sanctuary – A 4000 sq ft Forest Retreat Tucked away at the end of a spectacu ...

    From $538 per night (USD)

    Expedia

    Details
  • Dock & Sunset Views! Waterfront Thompson Getaway
    From $245 per night (USD)

    VRBO

    Dock & Sunset Views! Waterfront Thompson Getaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Escape to a peaceful lakefront lifestyle at this Thompson vacation rental on Little Pond! Ideal for families or a quiet ...

    From $245 per night (USD)

    VRBO

    Details