Vacation rentals in Orleans, MA

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Orleans, MA

The Gould Cape House - Orleans, MA

The Gould Cape House

Holiday Home, Orleans

The Gould Cape House is a holiday home in Orleans. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About The Gould Cape House

The Gould Cape House is a holiday home in Orleans. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,568.

From$384/night
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Summer Daydream - Orleans, MA

Summer Daydream

Holiday Home, Orleans

Summer Daydream is a holiday home in Orleans, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Summer Daydream

Summer Daydream is a holiday home in Orleans, with pet-friendly space. 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, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,133.

From$431/night
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Adorable Cape Cottage Near Kingsbury Beach - Orleans, MA

Adorable Cape Cottage Near Kingsbury Beach

Cottage, Orleans

Adorable Cape Cottage Near Kingsbury Beach is a cottage in Orleans, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Adorable Cape Cottage Near Kingsbury Beach

Adorable Cape Cottage Near Kingsbury Beach is a cottage in Orleans, with 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,868.

From$267/night
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Cozy Cape Cottage with Beach Access - Orleans, MA

Cozy Cape Cottage with Beach Access

Cottage, Orleans

Cozy Cape Cottage with Beach Access is a cottage in Orleans, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Cape Cottage with Beach Access

Cozy Cape Cottage with Beach Access is a cottage in Orleans, with 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,868.

From$267/night
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Vacation rentals with a pool in Orleans, MA

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

Cottages at the Even'tide Resort - Orleans, MA

Cottages at the Even'tide Resort

Cottage, Orleans

Cottages at the Even'tide Resort is a cottage in Orleans, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Cottages at the Even'tide Resort

Cottages at the Even'tide Resort is a cottage in Orleans, 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,669.

From$333/night
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Winstead Inn - Orleans, MA

Winstead Inn

Guest House, Orleans

Winstead Inn is a guest house in Orleans, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Winstead Inn

Winstead Inn is a guest house in Orleans, with pool access 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 breakfast, pool, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,138.

From$392/night
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Pool Privileges at Ocean Edge Resort! (Fees Apply) - Orleans, MA

Pool Privileges at Ocean Edge Resort! (Fees Apply)

Condo, Orleans

Pool Privileges at Ocean Edge Resort! (Fees Apply) is a condo in Orleans, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Pool Privileges at Ocean Edge Resort! (Fees Apply)

Pool Privileges at Ocean Edge Resort! (Fees Apply) is a condo in Orleans, with pool access, 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: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,215.

From$459/night
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Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th - Orleans, MA

Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th

Holiday Home, Orleans

Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th is a holiday home in Orleans, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th

Luxury Waterfront Home with Pool and Dock NEW 5% Discount Until Feb. 28th is a holiday home in Orleans, with pool access, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,749.

From$1,536/night
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Vacation rentals with parking in Orleans, MA

Find vacation rentals that make arriving by car easier.

NEW listing: Fam-friendly East Orleans, mins to Nauset, Skaket Beach & downtown - Orleans, MA

NEW listing: Fam-friendly East Orleans, mins to Nauset, Skaket Beach & downtown

Holiday Home, Orleans

NEW listing: Fam-friendly East Orleans, mins to Nauset, Skaket Beach & downtown is a holiday home in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers…

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About NEW listing: Fam-friendly East Orleans, mins to Nauset, Skaket Beach & downtown

NEW listing: Fam-friendly East Orleans, mins to Nauset, Skaket Beach & downtown is a holiday home in Orleans, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,040.

From$434/night
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Long View Cottage Close to Nauset, Skaket, & Bakers Pond - Orleans, MA

Long View Cottage Close to Nauset, Skaket, & Bakers Pond

Holiday Home, Orleans

Long View Cottage Close to Nauset, Skaket, & Bakers Pond is a holiday home in Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Long View Cottage Close to Nauset, Skaket, & Bakers Pond

Long View Cottage Close to Nauset, Skaket, & Bakers Pond is a holiday home in Orleans, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,149.

From$450/night
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Nicely Renovated East Orleans Area Home Sleeps 10 - Orleans, MA

Nicely Renovated East Orleans Area Home Sleeps 10

Holiday Home, Orleans

Nicely Renovated East Orleans Area Home Sleeps 10 is a holiday home in Orleans, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Nicely Renovated East Orleans Area Home Sleeps 10

Nicely Renovated East Orleans Area Home Sleeps 10 is a holiday home in Orleans, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,168.

From$453/night
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3 Mi to Nauset Beach! Family Home w/ Private Yard - Orleans, MA

3 Mi to Nauset Beach! Family Home w/ Private Yard

Holiday Home, Orleans

3 Mi to Nauset Beach! Family Home w/ Private Yard is a holiday home in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 3 Mi to Nauset Beach! Family Home w/ Private Yard

3 Mi to Nauset Beach! Family Home w/ Private Yard is a holiday home in Orleans, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,500.

From$500/night
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Pet-friendly vacation rentals in Orleans, MA

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

Brewster 3 Bedroom getaway with plenty of green space! - Orleans, MA

Brewster 3 Bedroom getaway with plenty of green space!

Holiday Home, Orleans

Brewster 3 Bedroom getaway with plenty of green space! is a holiday home in Orleans, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Brewster 3 Bedroom getaway with plenty of green space!

Brewster 3 Bedroom getaway with plenty of green space! is a holiday home in Orleans, 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 $2,342.

From$335/night
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Charming Laid-Back Cape Escape - Orleans, MA

Charming Laid-Back Cape Escape

Holiday Home, Orleans

Charming Laid-Back Cape Escape is a holiday home in Orleans, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming Laid-Back Cape Escape

Charming Laid-Back Cape Escape is a holiday home in Orleans, 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 $2,680.

From$383/night
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Samara Tide | 3BR Walk to Bay Beach, Pet Friendly - Orleans, MA

Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Holiday Home, Orleans

Samara Tide · 3BR Walk to Bay Beach, Pet Friendly is a holiday home in Orleans, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Samara Tide · 3BR Walk to Bay Beach, Pet Friendly is a holiday home in Orleans, 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 $3,223.

From$460/night
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80 East 080-EL - Modern comfort and convenience in Eastham - Orleans, MA

80 East 080-EL - Modern comfort and convenience in Eastham

Holiday Home, Orleans

80 East 080-EL - Modern comfort and convenience in Eastham is a holiday home in Orleans, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About 80 East 080-EL - Modern comfort and convenience in Eastham

80 East 080-EL - Modern comfort and convenience in Eastham is a holiday home in Orleans, 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 $3,862.

From$552/night
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Vacation rentals with a kitchen in Orleans, MA

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

Waterfront Cottage On Minister's Pond W/ Private Beach, Dock, Rowboats - Orleans, MA

Waterfront Cottage On Minister's Pond W/ Private Beach, Dock, Rowboats

Cottage, Orleans

Waterfront Cottage On Minister's Pond W/ Private Beach, Dock, Rowboats is a cottage in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Waterfront Cottage On Minister's Pond W/ Private Beach, Dock, Rowboats

Waterfront Cottage On Minister's Pond W/ Private Beach, Dock, Rowboats is a cottage in Orleans, with easy beach 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,504.

From$358/night
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Ministers Pond Waterfront - Orleans, MA

Ministers Pond Waterfront

Holiday Home, Orleans

Ministers Pond Waterfront is a holiday home in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Ministers Pond Waterfront

Ministers Pond Waterfront is a holiday home in Orleans, with easy beach 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,512.

From$359/night
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3 Mi to Nauset Beach! Family Home w/ Private Yard - Orleans, MA

3 Mi to Nauset Beach! Family Home w/ Private Yard

Cottage, Orleans

3 Mi to Nauset Beach! Family Home w/ Private Yard is a cottage in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About 3 Mi to Nauset Beach! Family Home w/ Private Yard

3 Mi to Nauset Beach! Family Home w/ Private Yard is a cottage in Orleans, with easy beach 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,497.

From$509/night
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Skaket Beach Area Home Sleeps 8 - Orleans, MA

Skaket Beach Area Home Sleeps 8

Holiday Home, Orleans

Skaket Beach Area Home Sleeps 8 is a holiday home in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Skaket Beach Area Home Sleeps 8

Skaket Beach Area Home Sleeps 8 is a holiday home in Orleans, with easy beach 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,613.

From$516/night
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Family-friendly vacation rentals in Orleans, MA

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

Studio Cottage w/ Oak Floors and Knotty Pine Walls (CS0003) - Orleans, MA

Studio Cottage w/ Oak Floors and Knotty Pine Walls (CS0003)

Cottage, Orleans

Studio Cottage w/ Oak Floors and Knotty Pine Walls (CS0003) is a cottage in Orleans, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the…

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About Studio Cottage w/ Oak Floors and Knotty Pine Walls (CS0003)

Studio Cottage w/ Oak Floors and Knotty Pine Walls (CS0003) is a cottage in Orleans, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,243.

From$178/night
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Lakefront Cottage in Eastham, near ocean and Bay - Orleans, MA

Lakefront Cottage in Eastham, near ocean and Bay

Cottage, Orleans

Lakefront Cottage in Eastham, near ocean and Bay is a cottage in Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lakefront Cottage in Eastham, near ocean and Bay

Lakefront Cottage in Eastham, near ocean and Bay is a cottage in Orleans, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,555.

From$222/night
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Quaint Cape Cottage Close to the Beach - Orleans, MA

Quaint Cape Cottage Close to the Beach

Cottage, Orleans

Quaint Cape Cottage Close to the Beach is a cottage in Orleans, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Quaint Cape Cottage Close to the Beach

Quaint Cape Cottage Close to the Beach is a cottage in Orleans, with 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,868.

From$267/night
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Waterfront Cottage on Private Pond minutes from the Ocean and Bay - Orleans, MA

Waterfront Cottage on Private Pond minutes from the Ocean and Bay

Cottage, Orleans

Waterfront Cottage on Private Pond minutes from the Ocean and Bay is a cottage in Orleans, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront Cottage on Private Pond minutes from the Ocean and Bay

Waterfront Cottage on Private Pond minutes from the Ocean and Bay is a cottage in Orleans, with 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, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,362.

From$337/night
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