Vacation rentals in Winchester, NH

Best Vacation rentals and Airbnb offers in Winchester, NH

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Apartment, Winchester

Studio w/ Trail Access ~ 10 Mi to Brattleboro! is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Studio w/ Trail Access ~ 10 Mi to Brattleboro! is a apartment in Winchester, 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 $904.

From$72/night

Show›

Lake-View Spofford Apartment w/ Shared Dock!

Apartment, Winchester

Lake-View Spofford Apartment w/ Shared Dock! is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Lake-View Spofford Apartment w/ Shared Dock!

Lake-View Spofford Apartment w/ Shared Dock! is a apartment in Winchester, 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 $1,182.

From$91/night

Show›

Lakeside Spofford Retreat Near Hiking & Boating!

Apartment, Winchester

Lakeside Spofford Retreat Near Hiking & Boating! is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Lakeside Spofford Retreat Near Hiking & Boating!

Lakeside Spofford Retreat Near Hiking & Boating! is a apartment in Winchester, 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 $1,191.

From$92/night

Show›

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Apartment, Winchester

Studio w/ Trail Access ~ 10 Mi to Brattleboro! is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Studio w/ Trail Access ~ 10 Mi to Brattleboro! is a apartment in Winchester, 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 $865.

From$102/night

Show›

Best Winchester, NH vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake

Cabin, Winchester

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake is a cabin in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

Read more

About Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake is a cabin in Winchester, 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,610.

From$400/night

Show›

The Carriage Barn Inn

B & B, Winchester

The Carriage Barn Inn is a b & b in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

Read more

About The Carriage Barn Inn

The Carriage Barn Inn is a b & b in Winchester, 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 breakfast, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,500.

From$197/night

Show›

The Tartan Fox at the Meadmere

B & B, Winchester

The Tartan Fox at the Meadmere is a b & b in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

Read more

About The Tartan Fox at the Meadmere

The Tartan Fox at the Meadmere is a b & b in Winchester, 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 cancellation, free breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,585.

From$209/night

Show›

Carriage Barn Inn

B & B, Winchester

Carriage Barn Inn is a b & b in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

Read more

About Carriage Barn Inn

Carriage Barn Inn is a b & b in Winchester, 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 cancellation, free breakfast, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,005.

From$244/night

Show›

Best Winchester, NH vacation rentals with a kitchen

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

The Burrell House

Guest House, Winchester

The Burrell House is a guest house in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About The Burrell House

The Burrell House is a guest house in Winchester, 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 $2,106.

From$270/night

Show›

Modern 6BR Home for Large Groups & Families

Holiday Home, Winchester

Modern 6BR Home for Large Groups & Families is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About Modern 6BR Home for Large Groups & Families

Modern 6BR Home for Large Groups & Families is a holiday home in Winchester, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,932.

From$539/night

Show›

Brand New: Forest Green Retreat in Brattleboro, VT

Holiday Home, Winchester

Brand New: Forest Green Retreat in Brattleboro, VT is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Brand New: Forest Green Retreat in Brattleboro, VT

Brand New: Forest Green Retreat in Brattleboro, VT is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. 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 $7,458.

From$860/night

Show›

Spacious Estate w/ Courtyard: 2 Miles to Downtown!

Cottage, Winchester

Spacious Estate w/ Courtyard: 2 Miles to Downtown! is a cottage in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Spacious Estate w/ Courtyard: 2 Miles to Downtown!

Spacious Estate w/ Courtyard: 2 Miles to Downtown! is a cottage in Winchester, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,960.

From$1,374/night

Show›

Our Favorite Family-Friendly Vacation Rentals in Winchester, NH

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

Downtown apartment ideal location to everything

Apartment, Winchester

Downtown apartment ideal location to everything is a apartment in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Downtown apartment ideal location to everything

Downtown apartment ideal location to everything is a apartment in Winchester, 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,851.

From$196/night

Show›

Waterfront Cottage on Scenic Sportsman Pond

Cottage, Winchester

Waterfront Cottage on Scenic Sportsman Pond is a cottage in Winchester, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond is a cottage in Winchester, with pet-friendly space, easy beach 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,427.

From$217/night

Show›

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Cottage, Winchester

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water is a cottage in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water is a cottage in Winchester, 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 $2,230.

From$250/night

Show›

Spacious 1763 updated family house in the town that time forgot

Holiday Home, Winchester

Spacious 1763 updated family house in the town that time forgot is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Spacious 1763 updated family house in the town that time forgot

Spacious 1763 updated family house in the town that time forgot is a holiday home in Winchester, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,980.

From$324/night

Show›