Vacation rentals in Osterville, MA

Best vacation rentals and Airbnb offers in Osterville, MA

Hyannis Beach House

Holiday Home, Osterville

Hyannis Beach House is a holiday home in Osterville, 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 Hyannis Beach House

Hyannis Beach House is a holiday home in Osterville, 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: ac, air conditioning, heating, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,190.

From$354/night

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New Seabury Escape

Holiday Home, Osterville

New Seabury Escape is a holiday home in Osterville, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About New Seabury Escape

New Seabury Escape is a holiday home in Osterville, 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, ourdoor pool, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,726.

From$382/night

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Sea Breeze Inn

Guest House, Osterville

Sea Breeze Inn is a guest house in Osterville, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Sea Breeze Inn

Sea Breeze Inn is a guest house in Osterville, 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 wifi, beachfront, beach front, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,001.

From$125/night

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New adorable one bedroom, one bath apartment unit. Private neighborhood beach, great location. Beach pass included.

Condo, Osterville

New adorable one bedroom, one bath apartment unit. Private neighborhood beach, great location. Beach pass included. is a condo in Osterville, with easy beach access, parking, and kitchen…

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About New adorable one bedroom, one bath apartment unit. Private neighborhood beach, great location. Beach pass included.

New adorable one bedroom, one bath apartment unit. Private neighborhood beach, great location. Beach pass included. is a condo in Osterville, 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 $2,303.

From$329/night

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Vacation rentals with a pool in Osterville, MA

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

Unit 44 Marsh & Ocean Views 3BD--A/C, Private Balcony, Association Beach & Pool

Condo, Osterville

Unit 44 Marsh & Ocean Views 3BD--A/C, Private Balcony, Association Beach & Pool is a condo in Osterville, with pool access, easy beach access, and outdoor space. This stay gives travelers a…

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About Unit 44 Marsh & Ocean Views 3BD--A/C, Private Balcony, Association Beach & Pool

Unit 44 Marsh & Ocean Views 3BD--A/C, Private Balcony, Association Beach & Pool is a condo in Osterville, with pool access, easy beach access, and outdoor space. 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 $2,395.

From$342/night

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Beautiful Cape Home Steps to Santuit Pond /Boating, Swimming, Fishing

Holiday Home, Osterville

Beautiful Cape Home Steps to Santuit Pond /Boating, Swimming, Fishing is a holiday home in Osterville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Beautiful Cape Home Steps to Santuit Pond /Boating, Swimming, Fishing

Beautiful Cape Home Steps to Santuit Pond /Boating, Swimming, Fishing is a holiday home in Osterville, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,465.

From$352/night

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The Breakwaters Hyannis - Your Home Away From Home RPAM069

Condo, Osterville

The Breakwaters Hyannis - Your Home Away From Home RPAM069 is a condo in Osterville, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About The Breakwaters Hyannis - Your Home Away From Home RPAM069

The Breakwaters Hyannis - Your Home Away From Home RPAM069 is a condo in Osterville, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,683.

From$383/night

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Lamb and Lion Inn

B & B, Osterville

Lamb and Lion Inn is a b & b in Osterville, 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 Lamb and Lion Inn

Lamb and Lion Inn is a b & b in Osterville, 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 $2,636.

From$329/night

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Vacation rentals with parking in Osterville, MA

Find vacation rentals that make arriving by car easier.

Ocean-View Gem w/ Private Beach in Mashpee!

Holiday Home, Osterville

Ocean-View Gem w/ Private Beach in Mashpee! is a holiday home in Osterville, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Ocean-View Gem w/ Private Beach in Mashpee!

Ocean-View Gem w/ Private Beach in Mashpee! is a holiday home in Osterville, 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, free wifi, parking, paid parking, and terrace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,377.

From$236/night

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2 Mi to Beach: Walkable Coastal Gem in Hyannis!

Holiday Home, Osterville

2 Mi to Beach: Walkable Coastal Gem in Hyannis! is a holiday home in Osterville, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 2 Mi to Beach: Walkable Coastal Gem in Hyannis!

2 Mi to Beach: Walkable Coastal Gem in Hyannis! is a holiday home in Osterville, 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, free wifi, parking, paid parking, and heating.

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

From$302/night

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Spacious Cape style home with partial lake views 3 bedroom, 2 bathroom Beach Pass Included

Holiday Home, Osterville

Spacious Cape style home with partial lake views 3 bedroom, 2 bathroom Beach Pass Included is a holiday home in Osterville, with easy beach access, parking, and kitchen access. This stay…

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About Spacious Cape style home with partial lake views 3 bedroom, 2 bathroom Beach Pass Included

Spacious Cape style home with partial lake views 3 bedroom, 2 bathroom Beach Pass Included is a holiday home in Osterville, 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 $2,394.

From$342/night

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Cozy Cape Escape Near Beaches & Dining

Holiday Home, Osterville

Cozy Cape Escape Near Beaches & Dining is a holiday home in Osterville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cozy Cape Escape Near Beaches & Dining

Cozy Cape Escape Near Beaches & Dining is a holiday home in Osterville, 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 $3,164.

From$452/night

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Pet-friendly vacation rentals in Osterville, MA

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

QUINTESSENTIAL COTTAGE IN BARNSTABLE VILLAGE

Holiday Home, Osterville

QUINTESSENTIAL COTTAGE IN BARNSTABLE VILLAGE is a holiday home in Osterville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About QUINTESSENTIAL COTTAGE IN BARNSTABLE VILLAGE

QUINTESSENTIAL COTTAGE IN BARNSTABLE VILLAGE is a holiday home in Osterville, 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 $2,294.

From$328/night

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18 Great Hill Rd - Pet-friendly home, close to pond beach and tennis

Holiday Home, Osterville

18 Great Hill Rd - Pet-friendly home, close to pond beach and tennis is a holiday home in Osterville, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About 18 Great Hill Rd - Pet-friendly home, close to pond beach and tennis

18 Great Hill Rd - Pet-friendly home, close to pond beach and tennis is a holiday home in Osterville, 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 $2,351.

From$336/night

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Modern Luxe on the Cape | Sleek Design, Central Air, Serene Views

Holiday Home, Osterville

Modern Luxe on the Cape · Sleek Design, Central Air, Serene Views is a holiday home in Osterville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Modern Luxe on the Cape | Sleek Design, Central Air, Serene Views

Modern Luxe on the Cape · Sleek Design, Central Air, Serene Views is a holiday home in Osterville, 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,721.

From$389/night

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HyannisPort 2BR Cottage w/ King, Queen & Twin Beds. Short walk to Ocean Beaches!

Cottage, Osterville

HyannisPort 2BR Cottage w/ King, Queen & Twin Beds. Short walk to Ocean Beaches! is a cottage in Osterville, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About HyannisPort 2BR Cottage w/ King, Queen & Twin Beds. Short walk to Ocean Beaches!

HyannisPort 2BR Cottage w/ King, Queen & Twin Beds. Short walk to Ocean Beaches! is a cottage in Osterville, 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 $2,816.

From$402/night

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Vacation rentals with a kitchen in Osterville, MA

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

Convenient Single-Level Retreat Near Harbor, Ferries & Main St Hyannis (2309)

Holiday Home, Osterville

Convenient Single-Level Retreat Near Harbor, Ferries & Main St Hyannis (2309) is a holiday home in Osterville, with kitchen access and a quieter setting. This stay gives travelers a…

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About Convenient Single-Level Retreat Near Harbor, Ferries & Main St Hyannis (2309)

Convenient Single-Level Retreat Near Harbor, Ferries & Main St Hyannis (2309) is a holiday home in Osterville, with 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: kitchen, with kitchen, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,112.

From$302/night

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2 Mi to Beach: Walkable Coastal Gem in Hyannis!

Holiday Home, Osterville

2 Mi to Beach: Walkable Coastal Gem in Hyannis! is a holiday home in Osterville, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 2 Mi to Beach: Walkable Coastal Gem in Hyannis!

2 Mi to Beach: Walkable Coastal Gem in Hyannis! is a holiday home in Osterville, 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,311.

From$330/night

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2 Mi to Beach: Walkable Coastal Gem in Hyannis!

Cottage, Osterville

2 Mi to Beach: Walkable Coastal Gem in Hyannis! is a cottage in Osterville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 2 Mi to Beach: Walkable Coastal Gem in Hyannis!

2 Mi to Beach: Walkable Coastal Gem in Hyannis! is a cottage in Osterville, 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 $3,155.

From$341/night

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Charming Ranch on the Cape

Holiday Home, Osterville

Charming Ranch on the Cape is a holiday home in Osterville, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Charming Ranch on the Cape

Charming Ranch on the Cape is a holiday home in Osterville, 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, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,144.

From$449/night

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Family-friendly vacation rentals in Osterville, MA

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

Home in HyannisPort/Craigville Bch 3BR/2BA: 5min to beach & Main St, linens, A/C

Holiday Home, Osterville

Home in HyannisPort/Craigville Bch 3BR/2BA: 5min to beach & Main St, linens, A/C is a holiday home in Osterville, with easy beach access, kitchen access, and room for a group. This stay…

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About Home in HyannisPort/Craigville Bch 3BR/2BA: 5min to beach & Main St, linens, A/C

Home in HyannisPort/Craigville Bch 3BR/2BA: 5min to beach & Main St, linens, A/C is a holiday home in Osterville, with easy beach access, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,836.

From$405/night

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Ocean Cottage for 2 —private!

Cottage, Osterville

Ocean Cottage for 2 —private! is a cottage in Osterville, 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 Ocean Cottage for 2 —private!

Ocean Cottage for 2 —private! is a cottage in Osterville, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,901.

From$414/night

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A Cotuit Escape- located on Main Street steps from Kettleer baseball park

Holiday Home, Osterville

A Cotuit Escape- located on Main Street steps from Kettleer baseball park is a holiday home in Osterville, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About A Cotuit Escape- located on Main Street steps from Kettleer baseball park

A Cotuit Escape- located on Main Street steps from Kettleer baseball park is a holiday home in Osterville, 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 $3,013.

From$430/night

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Book Your Last Minute Summer Vacation Now! 3 Night Min, 10% discount =>7 nights

Holiday Home, Osterville

Book Your Last Minute Summer Vacation Now! 3 Night Min, 10% discount =>7 nights is a holiday home in Osterville, with parking and kitchen access. This stay gives travelers a comfortable…

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About Book Your Last Minute Summer Vacation Now! 3 Night Min, 10% discount =>7 nights

Book Your Last Minute Summer Vacation Now! 3 Night Min, 10% discount =>7 nights is a holiday home in Osterville, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,074.

From$439/night

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