Osterville Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Osterville holiday rentals

Sun-loungers, beach towels

Pond View~ Abuts conservation and walking trails. There is fishing at the pond

Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Dennis
10.0 out of 10, Exceptional, (132 reviews)
"Very clean and well kept home. We had everything we needed. Will rent again in the future."
United States
Sara
The price is HK$1,411
HK$1,812 total
includes taxes & fees
4 Jun - 5 Jun
Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Interior

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"The view was breathe taking and the space was small yet comforting. The little label reminders were very helpful. The suggestion for things to were great. Wish week had more time to try the different places. Was an overall amazing stay would stay again."
United States
Theresa M.
The price is HK$1,528
HK$3,489 total
includes taxes & fees
4 Jun - 5 Jun
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Beach nearby, sun-loungers, beach towels

Walking distance to Private Beach! Charming Cottage North of Cape Cod.

Walking distance to Private Beach! Charming Cottage North of Cape Cod.
Wareham
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed the stay, would definitely come back!"
United States
Daniel W.
The price is HK$1,051
HK$3,993 total
includes taxes & fees
3 Jun - 4 Jun
Walking distance to Private Beach! Charming Cottage North of Cape Cod.
Exterior

Ocean View Room @ Beach Resort / Habitat *HOT TUB*

Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Cape Cod
The price is HK$784
HK$2,415 total
includes taxes & fees
7 Jun - 8 Jun
Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Exterior detail

Charming Antique Boathouse Located Directly On Long Pond.

Charming Antique Boathouse Located Directly On Long Pond.
Plymouth
9.8 out of 10, Exceptional, (112 reviews)
"The hosts were very accommodating. Our arrival was late, and it was easy to get into the boathouse."
United States
Mark P.
The price is HK$1,803
HK$2,854 total
includes taxes & fees
3 Jun - 4 Jun
Charming Antique Boathouse Located Directly On Long Pond.
Fridge, microwave, oven, stovetop

Cozy Riverfront Stay in Wareham

Cozy Riverfront Stay in Wareham
Wareham
10.0 out of 10, Exceptional, (3 reviews)
"Perfect for wedding guests. Spacious, clean and great viewWould definitely stay again"
United States
Karleen L.
The price is HK$1,111
HK$3,123 total
includes taxes & fees
3 Jun - 4 Jun
Cozy Riverfront Stay in Wareham
Sun-loungers, beach towels

Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
9.8 out of 10, Exceptional, (8 reviews)
"Great place! Great host!"
United States
Moira C.
The price is HK$1,122
HK$2,435 total
includes taxes & fees
4 Jun - 5 Jun
Make this charming, modern retreat your home away from home!!
Exterior

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
"Loved this property. "
United States
Carol S.
The price is HK$823
HK$3,815 total
includes taxes & fees
3 Jun - 4 Jun
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Terrace/patio

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (64 reviews)
"Great location and very nice apartment"
United States
Phil M.
The price is HK$588
HK$3,319 total
includes taxes & fees
3 Jun - 4 Jun
Quaint condo near private beach access with fireplace - close to dining
Interior

3 Mi to Beaches: Peaceful Wareham Getaway

3 Mi to Beaches: Peaceful Wareham Getaway
3.0 star property
Wareham
The price is HK$1,042
HK$2,048 total
includes taxes & fees
2 Jul - 3 Jul
3 Mi to Beaches: Peaceful Wareham Getaway
Exterior detail

The Blue Crab Unit 7

The Blue Crab Unit 7
Harwich
9.6 out of 10, Exceptional, (15 reviews)
"Nice place, decent central location "
United States
hannah k.
The price is HK$1,058
HK$1,866 total
includes taxes & fees
7 Jun - 8 Jun
The Blue Crab Unit 7
Outdoor dining

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
The price is HK$1,254
HK$5,105 total
includes taxes & fees
4 Jun - 5 Jun
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
TV

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (83 reviews)
"Host was super organized with clear instructions and easy check-in. The condo was well appointed and beautifully decorated. We enjoyed our brief stay!"
United States
Gina P.
The price is HK$853
HK$2,726 total
includes taxes & fees
17 Jun - 18 Jun
New Seabury Cape Condo + Pool & Beach Escape
Beach

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (113 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is HK$970
HK$2,500 total
includes taxes & fees
5 Jun - 6 Jun
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Beach nearby, sun-loungers, beach towels

Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!

Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!
Wareham
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is HK$1,129
HK$2,390 total
includes taxes & fees
4 Jun - 5 Jun
Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!
Terrace/patio

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (136 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is HK$1,959
HK$3,003 total
includes taxes & fees
3 Jun - 4 Jun
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Terrace/patio

The Captain's Quarters Suite Unit - 10

The Captain's Quarters Suite Unit - 10
Harwich
10.0 out of 10, Exceptional, (16 reviews)
"It was perfect for what I needed, hosts were helpful and accommodating. I would definitely stay here again!"
United States
Julienne
The price is HK$1,375
HK$2,274 total
includes taxes & fees
3 Jun - 4 Jun
The Captain's Quarters Suite Unit - 10
Beach nearby

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis
Brewster
9.0 out of 10, Wonderful, (20 reviews)
"Very nice accommodations. "
United States
Joseph D.
The price is HK$1,254
HK$4,674 total
includes taxes & fees
3 Jun - 4 Jun
Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis
Exterior

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Cape Cod
8.0 out of 10, Very good, (8 reviews)
"Cozy clean property that allows pets. Outdoor fire pit area was great and perfectly private. I also loved that the property had a private beach area with lounge chairs. I used the grill and had brunch on the patio table. So nice to enjoy the water from so many parts of the property. Area is quiet and a 7 min walk to Onset Center where you can grab icecream or on some weekdays there’s an even in town. Close to plazas for other needs."
United States
l E.
The price is HK$392
HK$4,085 total
includes taxes & fees
7 Jun - 8 Jun
The Crab Cottage@The Compound Beach Resort Habitat
Dining

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Dennis
10.0 out of 10, Exceptional, (11 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osterville Hotel Reviews

Cape Sands Inn

Cape Sands Inn

6/10 Okay
"The room was clean, the staff was OK but the surrounding part of the hotel was not well maintained. It did not look nice. I expected more."
June 1-night trip
Posted 2 hours ago
Cape Sands Inn

Find out more about Osterville

Search for holiday rentals in Osterville on Expedia! You can easily find your home rentals, villas, holiday apartments in Osterville using one of the methods below:

  • View our selection of featured holiday rentals in Osterville
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  • Enter your travel dates to view the best deals on holiday rentals in Osterville while they last

Look no further and take a look at our great range of rental properties in Osterville!

Frequently asked questions

Can I find holiday rentals in Osterville?

Yes, there are holiday rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osterville has to offer?

Charming 3 bed room with magnificent views & large deck: This holiday home rental outside of Osterville is equipped with a patio, air conditioning and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a stovetop, a microwave and an electric kettle, so that you can cook with friends or family.

How many holiday rentals are there in Osterville?

With 63 Expedia holiday rentals, you're guaranteed to find just the right place for your Osterville stay.

What’s there to see and do in Osterville?

Cape Cod Beaches and Dowses Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Stand Up & Paddle Cape Cod. Public Beach and Main Street are a couple of places you'll find in the wider area.

What’s a holiday rental in Osterville like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osterville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.