Osterville Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Osterville holiday rentals

Smart TV, books

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (25 reviews)
"Lovely house with nice location."
United States
amy d.
The price is HK$997
HK$5,373 total
includes taxes & fees
28 Mar - 29 Mar
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
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, (6 reviews)
"Great stay. Clean, comfortable, and exactly as listed. Perfect location with a great backyard to grill or sit by the fire pit. Check-in was easy and the host was very responsive. Would definitely book again!!"
United States
Laura D.
The price is HK$1,048
HK$2,289 total
includes taxes & fees
29 Mar - 30 Mar
Make this charming, modern retreat your home away from home!!
Smart TV

Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed

Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here four days. This house is centrally located and in a good, safe neighborhood. It was clean and had all supplies needed such as towels, dish soap, laundry soap, paper towels etc.Would stay here again. "
United States
Todd M.
Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed
Exterior

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

Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Cape Cod
The price is HK$782
HK$2,409 total
includes taxes & fees
29 Mar - 30 Mar
Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Interior

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (52 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is HK$774
HK$1,495 total
includes taxes & fees
30 Mar - 31 Mar
The Nantucket Room Unit - #2
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)
"Kitchen could use a k cup coffee maker and large frying pan. Light bulb on microwave was out. Clock on stove was broken and the stove said hot surface even when it was never turned. Upstairs toilet kept running. Basement carpet had some stains. All just minor things that need attention. Overall really loved the place. Hope to come back next year!"
United States
Stephen V.
The price is HK$1,032
HK$4,631 total
includes taxes & fees
30 Mar - 31 Mar
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Property grounds

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
8.8 out of 10, Excellent, (3 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is HK$977
HK$2,493 total
includes taxes & fees
29 Mar - 30 Mar
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
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, (3 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is HK$1,448
HK$3,422 total
includes taxes & fees
30 Mar - 31 Mar
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Pool

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is HK$1,165
HK$3,947 total
includes taxes & fees
27 Mar - 28 Mar
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Cape Cod
7.4 out of 10, Good, (6 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$195
HK$3,724 total
includes taxes & fees
16 Apr - 17 Apr
The Crab Cottage@The Compound Beach Resort Habitat
Smart TV, fireplace, books

Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod
South Yarmouth
10.0 out of 10, Exceptional, (13 reviews)
"Great location and very comfortable rental home. Everything you need is included and the house is well stocked and clean!"
United States
Dennis S.
The price is HK$1,506
HK$4,622 total
includes taxes & fees
27 Mar - 28 Mar
Modern Beach & Pond Getaway; Heart of Cape Cod
Exterior

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (23 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is HK$1,119
HK$3,014 total
includes taxes & fees
27 Mar - 28 Mar
Spacious and Bright , Very Close to Beach!
Beach nearby

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, (63 reviews)
"Very nice location and the unit was clean and comfortable. "
United States
Jeanne M.
The price is HK$469
HK$3,020 total
includes taxes & fees
28 Mar - 29 Mar
Quaint condo near private beach access with fireplace - close to dining
Property grounds

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is HK$2,345
HK$4,859 total
includes taxes & fees
27 Mar - 28 Mar
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Exterior detail

Harbor Getaway Unit- #1

Harbor Getaway Unit- #1
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"Quaint room, exactly as advertised. Easy to check in. I would recommend this inn to others."
United States
Ashley H.
The price is HK$774
HK$1,456 total
includes taxes & fees
30 Mar - 31 Mar
Harbor Getaway Unit- #1
Exterior

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is HK$1,407
HK$3,839 total
includes taxes & fees
29 Mar - 30 Mar
Falmouth Oasis
Dining

Big Sandy Beachcomber

Big Sandy Beachcomber
Ponds of Plymouth
9.6 out of 10, Exceptional, (14 reviews)
"Our stay was perfect! The house was clean and the host very responsive throughout! Would definitely stay again!"
United States
Ben L.
The price is HK$1,556
HK$3,703 total
includes taxes & fees
6 Apr - 7 Apr
Big Sandy Beachcomber
Beach nearby

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (43 reviews)
"Great place!"
United States
Michael P.
The price is HK$1,752
HK$3,025 total
includes taxes & fees
28 Mar - 29 Mar
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Interior

New Home in the heart of South Dennis

New Home in the heart of South Dennis
Dennis
9.8 out of 10, Exceptional, (12 reviews)
"Lovely home in a great location. Would rent this house again!"
United States
Jolie F.
The price is HK$1,223
HK$5,686 total
includes taxes & fees
28 Mar - 29 Mar
New Home in the heart of South Dennis
Terrace/patio

The Captain's Quarters Suite Unit - 10

The Captain's Quarters Suite Unit - 10
Harwich
10.0 out of 10, Exceptional, (15 reviews)
"Great property! Very nicely done apartment with easy access to town,restaurants,bike shop and supermarket. Our interaction with the owner was also great. Highly recommend this rental. The owner made the whole rental easy. "
United States
tom c.
The price is HK$774
HK$1,495 total
includes taxes & fees
26 Apr - 27 Apr
The Captain's Quarters Suite Unit - 10
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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

8/10 Good
"Hotel was clean and well decorated. Room had Keurig with coffee and tea pods as well as needed condiments for such. Bath items like a robe, shampoo, soap, moisturizer are provided along with plenty of fresh towels. Child enjoyed the splash pad and lazy river. A tad busy right after school, less crowded after dinner time. The arcade had plenty of games, prize machine was limited for larger ticket amount but run by Ryan Amusements and cards are interchangeable at various places. Restaurants on site and also fairly decent, better than I had expected actually. Overall a nice stay with my son and would return with him again. "
Jennifer 1-night trip
Posted 1 day ago
Margaritaville Resort Cape Cod

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
  • Use the map to find apartments and other holiday homes in the Osterville neighbourhood you prefer
  • 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?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This holiday home rental outside of Osterville is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.