Vacation rentals in Pleasant Bay, MA

Best vacation rentals and Airbnb offers in Pleasant Bay, MA

Riviera Sunset

Holiday Home, Pleasant Bay

Riviera Sunset is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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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Herring Brook

Holiday Home, Pleasant Bay

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

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About Herring Brook

Herring Brook is a holiday home in Pleasant Bay, 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 $4,050.

From$338/night

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Areys Pond Point

Holiday Home, Pleasant Bay

Areys Pond Point is a holiday home in Pleasant Bay. 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 Pleasant Bay. 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.

Apartment, Pleasant Bay

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach. is a apartment in Pleasant Bay, 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 Pleasant Bay, 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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Waterfront vacation rentals in Pleasant Bay, MA

Discover vacation rentals close to the coast, water, and beach areas around Pleasant Bay, MA.

Walk to Nauset Beach NEW AC System

Holiday Home, Pleasant Bay

Walk to Nauset Beach NEW AC System is a holiday home in Pleasant Bay, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Walk to Nauset Beach NEW AC System

Walk to Nauset Beach NEW AC System is a holiday home in Pleasant Bay, with 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, parking, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,381.

From$376/night

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Orleans Beach Retreat

Holiday Home, Pleasant Bay

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

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About Orleans Beach Retreat

Orleans Beach Retreat is a holiday home in Pleasant Bay, 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!

Holiday Home, Pleasant Bay

The Perfect Beach Getaway! is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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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Walk to the beach at Little Pleasant Bay from this newly decorated cottage!

Condo, Pleasant Bay

Walk to the beach at Little Pleasant Bay from this newly decorated cottage! is a condo in Pleasant Bay, with pet-friendly space and easy beach access. This stay gives travelers a…

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About Walk to the beach at Little Pleasant Bay from this newly decorated cottage!

Walk to the beach at Little Pleasant Bay from this newly decorated cottage! is a condo in Pleasant Bay, with pet-friendly space 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: pet friendly, pets friendly, washer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,255.

From$465/night

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Vacation rentals with a pool in Pleasant Bay, MA

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

Winstead Inn

Guest House, Pleasant Bay

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

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About Winstead Inn

Winstead Inn is a guest house in Pleasant Bay, 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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Lovely full remodel with pool walk to 3 beaches - dog friendly w permission

Cottage, Pleasant Bay

Lovely full remodel with pool walk to 3 beaches - dog friendly w permission is a cottage in Pleasant Bay, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Lovely full remodel with pool walk to 3 beaches - dog friendly w permission

Lovely full remodel with pool walk to 3 beaches - dog friendly w permission is a cottage in Pleasant Bay, with pet-friendly space, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,264.

From$895/night

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5-bedroom Cape with a pool and yard games.

Holiday Home, Pleasant Bay

5-bedroom Cape with a pool and yard games. is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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

B & B, Pleasant Bay

Ship's Knees Inn is a b & b in Pleasant Bay, 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 Pleasant Bay, 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 Pleasant Bay, MA

Find vacation rentals that make arriving by car easier.

Great Location Near Cape Cod National Seashore

Holiday Home, Pleasant Bay

Great Location Near Cape Cod National Seashore is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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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Bed, Splash Beyond – Coastal Comfort Awaits

Holiday Home, Pleasant Bay

Bed, Splash Beyond – Coastal Comfort Awaits is a holiday home in Pleasant Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Bed, Splash Beyond – Coastal Comfort Awaits

Bed, Splash Beyond – Coastal Comfort Awaits is a holiday home in Pleasant Bay, 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, and fishing.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,843.

From$320/night

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Bed, Splash & Beyond – Coastal Comfort Awaits

Holiday Home, Pleasant Bay

Bed, Splash & Beyond – Coastal Comfort Awaits is a holiday home in Pleasant Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Bed, Splash & Beyond – Coastal Comfort Awaits

Bed, Splash & Beyond – Coastal Comfort Awaits is a holiday home in Pleasant Bay, 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 $2,366.

From$338/night

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Spacious Harwich Haven Near Round Cove (1116)

Holiday Home, Pleasant Bay

Spacious Harwich Haven Near Round Cove (1116) is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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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Pet-friendly vacation rentals in Pleasant Bay, MA

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

Pet-Friendly Orleans Ranch (1560)

Holiday Home, Pleasant Bay

Pet-Friendly Orleans Ranch (1560) is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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

Holiday Home, Pleasant Bay

15 min Walk to Nauset Beach is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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!

Holiday Home, Pleasant Bay

15 min Walk to Nauset Beach! is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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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The Perfect Beach Getaway

Holiday Home, Pleasant Bay

The Perfect Beach Getaway is a holiday home in Pleasant Bay, 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 Pleasant Bay, 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 $3,657.

From$404/night

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Vacation rentals with a kitchen in Pleasant Bay, MA

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

Cute clapboard cottage on the hill off Stage Island Road!

Cottage, Pleasant Bay

Cute clapboard cottage on the hill off Stage Island Road! is a cottage in Pleasant Bay, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cute clapboard cottage on the hill off Stage Island Road!

Cute clapboard cottage on the hill off Stage Island Road! is a cottage in Pleasant Bay, 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, onsite parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,061.

From$294/night

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Sweet clapboard cottage that is walk to the beach and downtown!

Cottage, Pleasant Bay

Sweet clapboard cottage that is walk to the beach and downtown! is a cottage in Pleasant Bay, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Sweet clapboard cottage that is walk to the beach and downtown!

Sweet clapboard cottage that is walk to the beach and downtown! is a cottage in Pleasant Bay, 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: kitchen, with kitchen, washer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,061.

From$294/night

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Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Apartment, Pleasant Bay

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home is a apartment in Pleasant Bay, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home is a apartment in Pleasant Bay, 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 $2,255.

From$322/night

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

Apartment, Pleasant Bay

Perfect couples escape. Close to beaches, great biking & walking & pet friendly. is a apartment in Pleasant Bay, 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 Pleasant Bay, 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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