Vacation rentals in Windham, VT

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Windham, VT

Magic Birch Lodge - Windham, VT

Magic Birch Lodge

Holiday Home, Windham

Magic Birch Lodge is a holiday home in Windham, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Magic Birch Lodge

Magic Birch Lodge is a holiday home in Windham, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,044.

From$102/night
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Potter's Place - Windham, VT

Potter's Place

Holiday Home, Windham

Potter's Place is a holiday home in Windham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Potter's Place

Potter's Place is a holiday home in Windham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,254.

From$127/night
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Cozy Cabin in the Woods - Windham, VT

Cozy Cabin in the Woods

Holiday Home, Windham

Cozy Cabin in the Woods is a holiday home in Windham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy Cabin in the Woods

Cozy Cabin in the Woods is a holiday home in Windham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,507.

From$134/night
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Stratton Mountain On A Budget - Windham, VT

Stratton Mountain On A Budget

Apartment, Windham

Stratton Mountain On A Budget is a apartment in Windham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Stratton Mountain On A Budget

Stratton Mountain On A Budget is a apartment in Windham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $993.

From$142/night
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Vacation rentals with a pool in Windham, VT

Add a pool to the search when you want an easy place to cool off between outings.

Vantage Point #8 - Windham, VT

Vantage Point #8

Apartment, Windham

Vantage Point #8 is a apartment in Windham, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Vantage Point #8

Vantage Point #8 is a apartment in Windham, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,295.

From$125/night
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Mtn. view, easy access to village - Windham, VT

Mtn. view, easy access to village

Condo, Windham

Mtn. view, easy access to village is a condo in Windham, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Mtn. view, easy access to village

Mtn. view, easy access to village is a condo in Windham, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,618.

From$231/night
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Experience Stratton Mountain Resort just steps away - Windham, VT

Experience Stratton Mountain Resort just steps away

Condo, Windham

Experience Stratton Mountain Resort just steps away is a condo in Windham, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Experience Stratton Mountain Resort just steps away

Experience Stratton Mountain Resort just steps away is a condo in Windham, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,691.

From$242/night
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Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI - Windham, VT

Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI

Cabin, Windham

Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI is a cabin in Windham, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI

Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI is a cabin in Windham, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,898.

From$271/night
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Vacation rentals with parking in Windham, VT

Find vacation rentals that make arriving by car easier.

Sage House at Camp Greenwood Vermont with Sauna - Windham, VT

Sage House at Camp Greenwood Vermont with Sauna

Cabin, Windham

Sage House at Camp Greenwood Vermont with Sauna is a cabin in Windham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Sage House at Camp Greenwood Vermont with Sauna

Sage House at Camp Greenwood Vermont with Sauna is a cabin in Windham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,506.

From$215/night
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Thistle House at Camp Greenwood Vermont with Sauna - Windham, VT

Thistle House at Camp Greenwood Vermont with Sauna

Cabin, Windham

Thistle House at Camp Greenwood Vermont with Sauna is a cabin in Windham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Thistle House at Camp Greenwood Vermont with Sauna

Thistle House at Camp Greenwood Vermont with Sauna is a cabin in Windham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,506.

From$215/night
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Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you! - Windham, VT

Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Cabin, Windham

Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you! is a cabin in Windham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you! is a cabin in Windham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,785.

From$255/night
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Peaceful 5-BR Escape Near Stratton - Windham, VT

Peaceful 5-BR Escape Near Stratton

Holiday Home, Windham

Peaceful 5-BR Escape Near Stratton is a holiday home in Windham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Peaceful 5-BR Escape Near Stratton

Peaceful 5-BR Escape Near Stratton is a holiday home in Windham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,052.

From$436/night
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Pet-friendly vacation rentals in Windham, VT

Bring your pet along with stays that welcome four-legged travelers.

Dog friendly, near Stratton, Magic & Bromley - Windham, VT

Dog friendly, near Stratton, Magic & Bromley

Apartment, Windham

Dog friendly, near Stratton, Magic & Bromley is a apartment in Windham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dog friendly, near Stratton, Magic & Bromley

Dog friendly, near Stratton, Magic & Bromley is a apartment in Windham, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,457.

From$208/night
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Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets. - Windham, VT

Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.

Condo, Windham

Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets. is a condo in Windham, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.

Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets. is a condo in Windham, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,970.

From$281/night
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Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover - Windham, VT

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Holiday Home, Windham

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover is a holiday home in Windham, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers…

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About Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover is a holiday home in Windham, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,043.

From$292/night
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Derry Woods Cabin: Views | Deck | Lowell Lake - Windham, VT

Derry Woods Cabin: Views | Deck | Lowell Lake

Holiday Home, Windham

Derry Woods Cabin: Views · Deck · Lowell Lake is a holiday home in Windham, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Derry Woods Cabin: Views | Deck | Lowell Lake

Derry Woods Cabin: Views · Deck · Lowell Lake is a holiday home in Windham, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,672.

From$382/night
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Vacation rentals with a kitchen in Windham, VT

Compare stays with kitchen access for longer trips and easier meals.

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester - Windham, VT

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Cabin, Windham

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester is a cabin in Windham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester is a cabin in Windham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,740.

From$249/night
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Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16 - Windham, VT

Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16

Apartment, Windham

Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16 is a apartment in Windham, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16

Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16 is a apartment in Windham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,172.

From$310/night
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Cozy Ski-In/Ski-Out Condo on Magic Mountain - Windham, VT

Cozy Ski-In/Ski-Out Condo on Magic Mountain

Condo, Windham

Cozy Ski-In/Ski-Out Condo on Magic Mountain is a condo in Windham, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy Ski-In/Ski-Out Condo on Magic Mountain

Cozy Ski-In/Ski-Out Condo on Magic Mountain is a condo in Windham, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,201.

From$314/night
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Historic Vermont Farmhouse on 12 Acres, Quaint Vermont Experience - Windham, VT

Historic Vermont Farmhouse on 12 Acres, Quaint Vermont Experience

Holiday Home, Windham

Historic Vermont Farmhouse on 12 Acres, Quaint Vermont Experience is a holiday home in Windham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Historic Vermont Farmhouse on 12 Acres, Quaint Vermont Experience

Historic Vermont Farmhouse on 12 Acres, Quaint Vermont Experience is a holiday home in Windham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,665.

From$381/night
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Family-friendly vacation rentals in Windham, VT

Plan a trip with stays that give families more room to spread out.

Family/Pet Friendly Cabin w/ Modern Upgrades: Minutes to Mountains, Farms, Lake - Windham, VT

Family/Pet Friendly Cabin w/ Modern Upgrades: Minutes to Mountains, Farms, Lake

Holiday Home, Windham

Family/Pet Friendly Cabin w/ Modern Upgrades: Minutes to Mountains, Farms, Lake is a holiday home in Windham, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Family/Pet Friendly Cabin w/ Modern Upgrades: Minutes to Mountains, Farms, Lake

Family/Pet Friendly Cabin w/ Modern Upgrades: Minutes to Mountains, Farms, Lake is a holiday home in Windham, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,481.

From$212/night
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Cozy Vermont Escape w/ Deck, Near Skiing! - Windham, VT

Cozy Vermont Escape w/ Deck, Near Skiing!

Cottage, Windham

Cozy Vermont Escape w/ Deck, Near Skiing! is a cottage in Windham, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Vermont Escape w/ Deck, Near Skiing!

Cozy Vermont Escape w/ Deck, Near Skiing! is a cottage in Windham, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,225.

From$261/night
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Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT - Windham, VT

Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT

Holiday Home, Windham

Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT is a holiday home in Windham, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT

Fabulous 3-bedroom townhome at the base of Magic Mountain in Londonderry, VT is a holiday home in Windham, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,975.

From$425/night
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The Aster Chalet: a modern family retreat - Windham, VT

The Aster Chalet: a modern family retreat

Holiday Home, Windham

The Aster Chalet: a modern family retreat is a holiday home in Windham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About The Aster Chalet: a modern family retreat

The Aster Chalet: a modern family retreat is a holiday home in Windham, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,132.

From$447/night
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