Vacation rentals in South Orleans, MA

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in South Orleans, MA

Riviera Sunset - South Orleans, MA

Riviera Sunset

Holiday Home, South Orleans

Riviera Sunset is a holiday home in South Orleans, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Riviera Sunset

Riviera Sunset is a holiday home in South Orleans, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: beachfront, beach front, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,230.

From$273/night
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Areys Pond Point - South Orleans, MA

Areys Pond Point

Holiday Home, South Orleans

Areys Pond Point is a holiday home in South 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 Areys Pond Point

Areys Pond Point is a holiday home in South 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, internet, and bbq facilities.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,461.

From$480/night
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Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach. - South Orleans, MA

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.

Apartment, South Orleans

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach. is a apartment in South Orleans, with easy beach access and a quieter setting. This stay gives travelers a…

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About Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach. is a apartment in South Orleans, with easy beach 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,718.

From$245/night
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Come enjoy Orleans and Chatham - South Orleans, MA

Come enjoy Orleans and Chatham

Holiday Home, South Orleans

Come enjoy Orleans and Chatham is a holiday home in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Come enjoy Orleans and Chatham

Come enjoy Orleans and Chatham is a holiday home in South 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,012.

From$287/night
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Vacation rentals with a pool in South Orleans, MA

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

Winstead Inn - South Orleans, MA

Winstead Inn

Guest House, South Orleans

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

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About Winstead Inn

Winstead Inn is a guest house in South 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 $2,822.

From$352/night
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Sunny, single level Susanna Village patio home with golf course views and pool access. - South Orleans, MA

Sunny, single level Susanna Village patio home with golf course views and pool access.

Condo, South Orleans

Sunny, single level Susanna Village patio home with golf course views and pool access. is a condo in South Orleans, with pool access, outdoor space, and kitchen access. This stay gives…

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About Sunny, single level Susanna Village patio home with golf course views and pool access.

Sunny, single level Susanna Village patio home with golf course views and pool access. is a condo in South Orleans, with pool access, outdoor 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: pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,006.

From$429/night
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5-bedroom Cape with a pool and yard games. - South Orleans, MA

5-bedroom Cape with a pool and yard games.

Holiday Home, South Orleans

5-bedroom Cape with a pool and yard games. is a holiday home in South Orleans, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About 5-bedroom Cape with a pool and yard games.

5-bedroom Cape with a pool and yard games. is a holiday home in South Orleans, 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: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,476.

From$1,068/night
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Ship's Knees Inn - South Orleans, MA

Ship's Knees Inn

B & B, South Orleans

Ship's Knees Inn is a b & b in South Orleans, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Ship's Knees Inn

Ship's Knees Inn is a b & b in South Orleans, with pool access and easy beach 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 breakfast, pool, free wifi, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,829.

From$353/night
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Vacation rentals with parking in South Orleans, MA

Find vacation rentals that make arriving by car easier.

Nauset Heights Cozy Cottage - South Orleans, MA

Nauset Heights Cozy Cottage

Holiday Home, South Orleans

Nauset Heights Cozy Cottage is a holiday home in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Nauset Heights Cozy Cottage

Nauset Heights Cozy Cottage is a holiday home in South 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 $1,988.

From$284/night
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Cozy Cape Cottage - South Orleans, MA

Cozy Cape Cottage

Cottage, South Orleans

Cozy Cape Cottage is a cottage in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cozy Cape Cottage

Cozy Cape Cottage is a cottage in South 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,078.

From$297/night
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Spacious Harwich Haven Near Round Cove (1116) - South Orleans, MA

Spacious Harwich Haven Near Round Cove (1116)

Holiday Home, South Orleans

Spacious Harwich Haven Near Round Cove (1116) is a holiday home in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious Harwich Haven Near Round Cove (1116)

Spacious Harwich Haven Near Round Cove (1116) is a holiday home in South 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,729.

From$390/night
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Charming, Renovated 1870s Home with Private Beach - South Orleans, MA

Charming, Renovated 1870s Home with Private Beach

Holiday Home, South Orleans

Charming, Renovated 1870s Home with Private Beach is a holiday home in South Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming, Renovated 1870s Home with Private Beach

Charming, Renovated 1870s Home with Private Beach is a holiday home in South 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, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,898.

From$414/night
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Pet-friendly vacation rentals in South Orleans, MA

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

Pet-Friendly Orleans Ranch (1560) - South Orleans, MA

Pet-Friendly Orleans Ranch (1560)

Holiday Home, South Orleans

Pet-Friendly Orleans Ranch (1560) is a holiday home in South Orleans, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Pet-Friendly Orleans Ranch (1560)

Pet-Friendly Orleans Ranch (1560) is a holiday home in South Orleans, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,574.

From$368/night
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15 min Walk to Nauset Beach - South Orleans, MA

15 min Walk to Nauset Beach

Holiday Home, South Orleans

15 min Walk to Nauset Beach is a holiday home in South Orleans, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 15 min Walk to Nauset Beach

15 min Walk to Nauset Beach is a holiday home in South Orleans, with pet-friendly space, easy beach 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 cancellation, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,300.

From$369/night
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15 min Walk to Nauset Beach! - South Orleans, MA

15 min Walk to Nauset Beach!

Holiday Home, South Orleans

15 min Walk to Nauset Beach! is a holiday home in South Orleans, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the…

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About 15 min Walk to Nauset Beach!

15 min Walk to Nauset Beach! is a holiday home in South Orleans, with pet-friendly space, easy beach 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,653.

From$379/night
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Perfect couples escape. Close to beaches, great biking & walking & pet friendly. - South Orleans, MA

Perfect couples escape. Close to beaches, great biking & walking & pet friendly.

Apartment, South Orleans

Perfect couples escape. Close to beaches, great biking & walking & pet friendly. is a apartment in South Orleans, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Perfect couples escape. Close to beaches, great biking & walking & pet friendly.

Perfect couples escape. Close to beaches, great biking & walking & pet friendly. is a apartment in South 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,759.

From$394/night
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Vacation rentals with a kitchen in South Orleans, MA

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

Great Location Near Cape Cod National Seashore - South Orleans, MA

Great Location Near Cape Cod National Seashore

Holiday Home, South Orleans

Great Location Near Cape Cod National Seashore is a holiday home in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Great Location Near Cape Cod National Seashore

Great Location Near Cape Cod National Seashore is a holiday home in South 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,051.

From$293/night
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Quiet Neighborhood .2 miles to Skaket Beach (1193) - South Orleans, MA

Quiet Neighborhood .2 miles to Skaket Beach (1193)

Holiday Home, South Orleans

Quiet Neighborhood .2 miles to Skaket Beach (1193) is a holiday home in South Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Quiet Neighborhood .2 miles to Skaket Beach (1193)

Quiet Neighborhood .2 miles to Skaket Beach (1193) is a holiday home in South 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,399.

From$343/night
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Orleans Beach Retreat - South Orleans, MA

Orleans Beach Retreat

Holiday Home, South Orleans

Orleans Beach Retreat is a holiday home in South Orleans, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Orleans Beach Retreat

Orleans Beach Retreat is a holiday home in South 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 wifi, 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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The Perfect Beach Getaway! - South Orleans, MA

The Perfect Beach Getaway!

Holiday Home, South Orleans

The Perfect Beach Getaway! is a holiday home in South Orleans, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About The Perfect Beach Getaway!

The Perfect Beach Getaway! is a holiday home in South Orleans, with pet-friendly space, easy beach 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,952.

From$422/night
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Family-friendly vacation rentals in South Orleans, MA

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

Cozy Cottage - South Orleans, MA

Cozy Cottage

Cottage, South Orleans

Cozy Cottage is a cottage in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Cozy Cottage

Cozy Cottage is a cottage in South 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,190.

From$170/night
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Cozy Cottage in Eastham near National Seashore - South Orleans, MA

Cozy Cottage in Eastham near National Seashore

Cottage, South Orleans

Cozy Cottage in Eastham near National Seashore is a cottage in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Cottage in Eastham near National Seashore

Cozy Cottage in Eastham near National Seashore is a cottage in South 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,609.

From$230/night
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Eastham Cottage with AC and Private Back Yard (2217) - South Orleans, MA

Eastham Cottage with AC and Private Back Yard (2217)

Cottage, South Orleans

Eastham Cottage with AC and Private Back Yard (2217) is a cottage in South Orleans, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Eastham Cottage with AC and Private Back Yard (2217)

Eastham Cottage with AC and Private Back Yard (2217) is a cottage in South 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,625.

From$232/night
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Cute Cottage Retreat 1/2 Mile to Weeset Point Beach - South Orleans, MA

Cute Cottage Retreat 1/2 Mile to Weeset Point Beach

Holiday Home, South Orleans

Cute Cottage Retreat 1/2 Mile to Weeset Point Beach is a holiday home in South Orleans, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cute Cottage Retreat 1/2 Mile to Weeset Point Beach

Cute Cottage Retreat 1/2 Mile to Weeset Point Beach is a holiday home in South 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 $1,927.

From$275/night
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