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Wireless Internet
Air conditioning
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Heated pool
Private indoor pool
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Private tennis court
Cot available
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Pool or snooker table
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Staffed property
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Pets
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Car not required

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Smoking - Ask
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Beach or lakeside relaxation
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
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Horse riding
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Golf course on site or within 15 min walk
Golf within 30mins drive
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656 Houses

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271 Westwind Cir

Osterville house

3 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$221

236B Smoke Valley Road 153791

Osterville house

3 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$465

Contemporary Gem with Private Pool!

Osterville house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$403

Walk to Joshua Pond Beach & Downtown!

Osterville house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$225

Great rentals within 20 miles that match your search

Skip to beach! Condo across from beach!

Dennis Port condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 1 hour 34 minutes

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Price per night from

$172

Sunset Bay Cottage Lg backyard w sunset views,Trails to Grays Bch, kayaks, bikes

Yarmouth Port house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$270

Ultimate Vacation Home

South Yarmouth hotel apartment

1 bedroom
1 bathroom

sleeps 5

Responds fast! avg. 3 hours 19 minutes

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Price per night from

$113

Walk to beach - 3 Bedroom cottage

Dennis Port house

3 bedrooms
1 bathroom

sleeps 6

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Price per night from

$246

Tidal View 6

East Sandwich cottage

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$129

Escape to Cape Cod - 4 Bedroom near Sound Beaches

South Yarmouth house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$548

18 Knott Avenue

Sandwich house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$170

Keyes Beach Retreat

Barnstable villa

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$514

Sea Beach House

Barnstable villa

5 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$570

Charming Beach House - Beautifully Updated & Immaculate. Walk to Nantucket Sound

South Chatham house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$429

Spectacular waterfront home with boat dock & private beach in a gated community

Hyannis house

5 bedrooms
5 bathrooms

sleeps 12

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Price per night from

$1,142

Spectacular Martha's Vineyard Island Home!

Oak Bluffs townhouse

3 bedrooms
3 bathrooms

sleeps 12

Responds fast! avg. 2 hours 16 minutes

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Price per night from

$451

Sagamore, Cape Cod Vacation Rental - Lovely old Cape known as the 'Rose Cottage'

Sagamore house

5 bedrooms
1 bathroom

sleeps 10

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$262

Immaculate - Spacious 4 Bed / 2 Bath Ranch (.5 miles to beach & attractions)

South Yarmouth house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$411

Treetops - Large House and Private Haven in Centerville Near Craigville Beach

Centerville house

4 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$571

Oceanfront CENTRAL A/C FamilyFriendly Home at Falmouth Heights Beach.2 KITCHENS

Falmouth house

6 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$1,085

Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs

Oak Bluffs house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$571

Spacious Falmouth Home sleeps 9, steps to Wood Neck Beach, Bike Path & Main St

Falmouth house

4 bedrooms
4 bathrooms

sleeps 9

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Price per night from

$743

Seascape Vacation Rental Dennis Port-OCEANFRONT PROPERTY-Sleeps 16 7BR/4BTH

Dennis Port house

7 bedrooms
5 bathrooms

sleeps 16

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Price per night from

$1,957

Walk to Private Beach

Falmouth studio

Studio
1 bathroom

sleeps 4

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Price per night from

$156

5 Star Beach House, Walk to Beach & Town, Immaculate Family Rental

Harwich Port house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$857

Beautifully decorated Brewster Home

Brewster house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$717

Vineyard Charming Retreat near beaches and center

Oak Bluffs house

3 bedrooms
2 bathrooms

sleeps 7

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$400

Beautifully renovated house steps from beach

West Yarmouth house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$467

Cape Cod Spacious 1BR Condo with Outdoor Sitting Area

New Seabury apartment

1 bedroom
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Cape Cod Vibrant 2BR Condo w Indoor Swimming Pool & Games Room

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Cape Cod Inviting 2BR Condo with Outdoor Sitting Area

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Private 2 BR Conso with Indoor Pool and Tennis Court Cape Cod

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Cape Cod Modern 2BR Condo with Indoor Swimming Pool

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Cape Cod Stylish 2BR Condo w Indoor Pool and Tennis Court

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Cozy 2BR Condo w Tennis Court & Outdoor Sitting Area- Cape Cod

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Magnificent 2BR Condo w Indoor Pool and Ping-Pong Table

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Stunning 2BR Condo Cape Cod with Tennis Court & Games Room

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Stunning 2BR Condo with Indoor Pool & Outdoor Sitting Area

New Seabury apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$294

Viewing 38 of 656
rentals in Osterville

Also consider

Dennis 266 properties
Eastham 178 properties
Chatham 177 properties
Orleans 140 properties
Sandwich 105 properties
Harwich 89 properties
Wellfleet 73 properties
Yarmouth 67 properties
Provincetown 52 properties
Falmouth 49 properties
Brewster 41 properties
Truro 28 properties
South Dennis 23 properties
Bourne 18 properties
Hyannis 16 properties
New Seabury 15 properties
Barnstable 13 properties
North Truro 13 properties
Centerville 11 properties
South Orleans 10 properties
Marstons Mills 10 properties
Mashpee 8 properties
Forestdale 5 properties
Cotuit 5 properties
North Eastham 5 properties
Cape Cod 1,437 properties
Nantucket 31 properties
Silver Beach 10 properties
Marlborough 8 properties
Quincy 6 properties
Salisbury 5 properties
Beverly 5 properties

Osterville Rentals

Per night

656 Houses

Viewing 38 of 656rentals in Osterville

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Viewing 38 of 656
rentals in Osterville