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Vacation Homes in Osterville

Find the vacation homes that appeal to you the most

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The best vacation homes in Osterville

Check out our selection of great vacation homes in Osterville

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Autumn Escape by the Cape 4 drm home

Mashpee (Near Osterville)

Featuring a garden, Autumn Escape by the Cape 4 drm home provides accommodations in Mashpee. This property offers access to a balcony, free private parking, and free Wifi.

S
Sarah
From
United States
This house is an absolute gem, clearly a cherished family vacation home filled with warmth and care. Brendon is such a kind host, and it’s obvious he genuinely enjoys sharing this space. The home is both beautiful and cozy, with thoughtful touches like heated floors in the first-floor bathroom. The location is perfect too, just minutes from some of the best beaches. Honestly, one of the best stays I’ve ever had.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
$1,006
1 night, 2 adults
Check availability

Cape Cod Hyannis Rendezvous'

Barnstable (Near Osterville)

A recently renovated vacation home, Cape Cod Hyannis Rendezvous' offers accommodations in Barnstable.

A
Ana
From
United States
Beautiful house, great location
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 10 reviews
Price from
$683
1 night, 2 adults
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Immaculate Beach Condo

Dennis Port (Near Osterville)

Immaculate Beach Condo is located in Dennis Port, just 23 miles from Cape Cod National Seashore and 24 miles from Sandwich Glass Museum.

L
Laura
From
United States
Great location, wonderful beach, walkable to the little cafe and shops in town
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 7 reviews
Price from
$380.17
1 night, 2 adults
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Scallop's Nest

Dennis Port (Near Osterville)

Scallop's Nest offers accommodations in Dennis Port, 23 miles from Cape Cod National Seashore and 23 miles from Sandwich Glass Museum.

L
Lisa
From
United States
We love this bright and cheery cottage! It is well stocked and thoughtfully provided with all the amenities. It has a great outdoor shower! This year, a beautiful new stove and refrigerator were added. It is a great location close to everything but with a very private setting.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 8 reviews
Price from
$480
1 night, 2 adults
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2 Minute Walk to Beach, Cape Cod Escape

Dennis Port (Near Osterville)

2 Minute Walk to Beach, Cape Cod Escape offers accommodations in Dennis Port, a 5-minute walk from Sea Street Beach and 21 miles from Nauset Lighthouse.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 10 reviews
Price from
$445
1 night, 2 adults
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Steps to Beaches & Main Street: Hyannis Retreat

Hyannis (Near Osterville)

Steps to Beaches & Main Street: Hyannis Retreat offers accommodations in Hyannis, a 18-minute walk from Veteran's Park beach and 16 miles from Sandwich Glass Museum.

E
Elena
From
Canada
We were absolutely stunned by the beauty of the house. Every detail was thoughtfully designed for a comfortable stay, and nothing was missing. The yard is beautifully maintained, and the cleanliness is impeccable. The amenities are amazing, and everything is perfectly organized. We are truly grateful for this wonderful experience!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 5 reviews
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Wedgewood Cottage

Barnstable (Near Osterville)

Wedgewood Cottage is located in Barnstable, just 12 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gardens.

I
Issam
From
Canada
Everything , very clean good management
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 12 reviews
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Renovated & Sophisticated Home Near Beach & Shops!

Barnstable (Near Osterville)

14 miles from Sandwich Glass Museum in Barnstable, Renovated & Sophisticated Home Near Beach & Shops! offers accommodations with access to a hot tub.

A
Ana
From
United States
Our stay was incredible. The host was very friendly and accommodating, making our stay extra special. The house was well located and clean, offering all the amenities needed on a daily basis. We'll definitely be back.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 45 reviews
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The Cape House

Cotuit (Near Osterville)

The Cape House offers accommodations in Cotuit, 11 miles from Sandwich Glass Museum and 11 miles from Heritage Museums & Gardens. The air-conditioned accommodation is a 11-minute walk from Ropes...

C
Christian
From
United States
Love the amenities. House is new all apliances are new. Beds are super comfy.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 7 reviews
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Bright & Open Central A C Dog Friendly

Barnstable (Near Osterville)

Bright & Open Central A C Dog Friendly offers accommodations in Barnstable, 24 miles from Plimoth Plantation.

A
Aimee
From
United States
The host went out of their way to make dog owners feel welcome.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 14 reviews
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All vacation homes in Osterville

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Osterville and surrounding area in the past month

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Popular with guests booking vacation homes in Osterville

Popular with guests booking vacation homes in Osterville

Popular with guests booking vacation homes in Hyannis

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 36 reviews

Popular with guests booking vacation homes in Barnstable

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 45 reviews

Popular with guests booking vacation homes in Barnstable

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 4 reviews

Popular with guests booking vacation homes in Barnstable

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Barnstable

Popular with guests booking vacation homes in Hyannis

Popular with guests booking vacation homes in Centerville

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 3 reviews

Popular with guests booking vacation homes in Barnstable

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews

Enjoy breakfast in Osterville and nearby

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Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

Swing Set Plunge pool and large yard await is located in Barnstable, just 1.5 miles from Long Beach and 14 miles from Sandwich Glass Museum.

Private Saltwater Pool Game Room near Beaches offers accommodations in Barnstable, 12 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gardens.

A 8-minute walk from Craigville Beach in Centerville, Bay Breeze Escape—Pool, Game Room Views features accommodations with access to a hot tub.

1.7 miles from Craigville Beach in Centerville, Bumps River Bungalow provides accommodations with access to a hot tub. This vacation home features accommodations with a patio.

Unique A Frame Short Drive to Beach offers accommodations in Barnstable, 1.7 miles from Craigville Beach and 12 miles from Sandwich Glass Museum.

Private Pool Central AC Dog Friendly is located in Barnstable, just 12 miles from Sandwich Glass Museum and 12 miles from Heritage Museums & Gardens.

1.6 miles from Craigville Beach in Barnstable, Cape Cod Village - Pool, Hot Tub & Fire Pit offers accommodations with access to a hot tub.

Waterfront Walk to Beach offers accommodations in Barnstable, 14 miles from Heritage Museums & Gardens and 29 miles from Plimoth Plantation.

Save money on vacation homes in Osterville and nearby – budget options available

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11 miles from Sandwich Glass Museum in Barnstable, Elegant Family Osterville Retreat Near Dowses Beach features accommodations with access to a fitness center.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Spacious Stone Fire Pit Game Room is located in Barnstable, just 27 miles from Plimoth Plantation and 7.7 miles from St Francis Xavier Church.

Wedgewood Cottage

Barnstable
Budget options available
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 12 reviews

Wedgewood Cottage is located in Barnstable, just 12 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gardens.

Relaxing Retreat just Minutes to Beach offers accommodations in Barnstable, 12 miles from Sandwich Glass Museum and 12 miles from Heritage Museums & Gardens.

Cozy Cape Escape Near Beaches Dining offers accommodations in Centerville, 12 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gardens.

Cape Cod Escape – 1 Mile to Beach, A/C Grill offers accommodations in Centerville, 1.2 miles from Craigville Beach and 12 miles from Sandwich Glass Museum.

Coastal Charm on the Cape

Centerville
Budget options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Coastal Charm on the Cape is located in Centerville, just 13 miles from Heritage Museums & Gardens and 30 miles from Plimoth Plantation.

Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 3 reviews

Golf & Unwind: Family Home 2 Mi to Covell’s Beach! offers accommodations in Centerville, 12 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gardens.

Vacation Homes with swimming pools in Osterville and nearby

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Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

11 miles from Sandwich Glass Museum in Centerville, Game Room + Patio: Quiet Centerville Beach Base features accommodations with access to a spa center.

Stay On The Cape Vacation Rentals: Large Family Home With Pool Come Enjoy The Cape is located in Barnstable, just 9.4 miles from Sandwich Glass Museum and 10 miles from Heritage Museums & Gardens.

Cape Castle

Mashpee
Swimming pool

12 miles from Sandwich Glass Museum in Mashpee, Cape Castle offers accommodations with access to a sauna and hot tub.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

A 14-minute walk from Orrin Keyes Beach in Barnstable, Cape Escape features accommodations with access to a hot tub. This property offers a private pool, free Wifi, and free private parking.

Family Retreat hot tub Firepit Beach nearby offers accommodations in Barnstable, 13 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gardens.

Plum Paradise offers accommodations in Barnstable, 11 miles from Heritage Museums & Gardens and 28 miles from Plimoth Plantation.

Featuring free bikes, Moon Compass Manor features accommodations in Sandwich. Guests can benefit from a patio and an outdoor pool. Outdoor seating is also available at the vacation home.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 36 reviews

The Cottages at Captain Gosnold Village in Hyannis provides accommodations with a seasonal outdoor swimming pool, a garden, and barbecue facilities.