Osterville Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Osterville holiday rentals

Private beach nearby, beach bar
The Club at New Seabury

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (340)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury
Exterior
The Crab Cottage@The Compound Beach Resort Habitat

Cabin in Wareham

The Crab Cottage@The Compound Beach Resort Habitat
7.4 out of 10, Good, (6)
"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$397
HK$4,037 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Crab Cottage@The Compound Beach Resort Habitat
On the beach, white sand
InnSeason Resorts Captain's Quarters

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
The price is HK$1,159
HK$1,326 total
includes taxes & fees
7 Jan - 8 Jan 2026
InnSeason Resorts Captain's Quarters
On the beach, sun-loungers, beach towels
The Bunk Room @ The Compound ~Fish-Hunt-Breakfast

Holiday Home in Wareham

The Bunk Room @ The Compound ~Fish-Hunt-Breakfast
2.0 star property
The price is HK$583
HK$1,397 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bunk Room @ The Compound ~Fish-Hunt-Breakfast
Exterior
Cozy Large Home in Harwich with Patio near Wequassett Resort

Holiday Home in Harwich

Cozy Large Home in Harwich with Patio near Wequassett Resort
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is HK$1,237
HK$4,031 total
includes taxes & fees
9 Jan - 10 Jan 2026
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Apartment in Onset

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
9.4 out of 10, Exceptional, (9)
"Great location"
United States
Robert C.
The price is HK$1,113
HK$2,998 total
includes taxes & fees
30 Dec - 31 Dec
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Holiday Home in Bass River

Charming House by the Beach with Patio, Grill, FirePit
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
The price is HK$1,159
HK$4,177 total
includes taxes & fees
25 Dec - 26 Dec
Charming House by the Beach with Patio, Grill, FirePit
Beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Holiday Home in Dennis

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is HK$1,003
HK$2,524 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Fridge, microwave, oven, stovetop
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Holiday Home in West Brewster

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
The price is HK$1,150
HK$5,571 total
includes taxes & fees
27 Dec - 28 Dec
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Indoor pool, outdoor pool
Brewster Green Resort

Aparthotel in Brewster

Brewster Green Resort
3.5 star property
9.4 out of 10, Exceptional, (121)
"Loved your location. We were originally placed in one of the townhomes, but when the locks/key didn't work, we were upgraded to the stand-alone house #106, which was wonderful! We loved the entire house - kitchen was great and stocked perfectly and all the rooms were big and comfortable. We hope to be back again soon!"
United States
Kathleen
The price is HK$1,392
HK$1,593 total
includes taxes & fees
25 Dec - 26 Dec
Brewster Green Resort
Interior
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Cottage in Dennis

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
9.6 out of 10, Exceptional, (177)
"Fenced in yard was perfect and close walk to both beach and restaurants."
United States
Mike Kayla B.
The price is HK$1,478
HK$2,724 total
includes taxes & fees
26 Dec - 27 Dec
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
Fridge, microwave, oven, stovetop
Oldest Town of Cape Cod In The Historic District

Holiday Home in Sandwich

Oldest Town of Cape Cod In The Historic District
9.0 out of 10, Wonderful, (17)
"We really loved this place and I "
United States
Valerie D.
The price is HK$778
HK$2,751 total
includes taxes & fees
6 Jan - 7 Jan 2026
Oldest Town of Cape Cod In The Historic District
Exterior
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Apartment in Onset

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
The price is HK$1,113
HK$2,998 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Property grounds
Big Sandy Beachcomber

Holiday Home in Ponds of Plymouth

Big Sandy Beachcomber
9.6 out of 10, Exceptional, (12)
"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$1,277
HK$3,373 total
includes taxes & fees
25 Dec - 26 Dec
Big Sandy Beachcomber
Exterior
Amazing Onset Getaway in the Starfish Suite

Condo in Onset

Amazing Onset Getaway in the Starfish Suite
9.8 out of 10, Exceptional, (24)
"Location was unbelievable-right next to beach"
United States
Terry B.
The price is HK$1,183
HK$3,293 total
includes taxes & fees
26 Dec - 27 Dec
Amazing Onset Getaway in the Starfish Suite
Fridge, microwave, oven, stovetop
Make this charming, modern retreat your home away from home!!

Holiday Home in Wareham

Make this charming, modern retreat your home away from home!!
9.6 out of 10, Exceptional, (5)
"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$1,159
HK$2,398 total
includes taxes & fees
5 Jan - 6 Jan 2026
Make this charming, modern retreat your home away from home!!
Outdoor dining
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Holiday Home in Dennis

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
The price is HK$693
HK$2,431 total
includes taxes & fees
28 Dec - 29 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Fridge, microwave, oven, stovetop
The Mermaid Cottage @ The Compound Beach Resort Habitat

Holiday Home in Wareham

The Mermaid Cottage @ The Compound Beach Resort Habitat
8.0 out of 10, Very good, (7)
"Love the place but felt like would of been better if the owner wasn’t around not that they where bad or annoying just didn’t feel like we was like away felt like we was being watched but besides that loved it Wish barbecue was working and speaker in house was weird set up but besides that it was amazing"
United States
Oscar B.
The price is HK$1,388
HK$5,374 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Mermaid Cottage @ The Compound Beach Resort Habitat
Terrace/patio
Gold Anchor Cottage - private hot tub getaway!

Holiday Home in Sandwich

Gold Anchor Cottage - private hot tub getaway!
10.0 out of 10, Exceptional, (5)
"Small cottage, but spacious vaulted ceilings and a great backyard hang out space with the hot tub. Close walk to public beach or parking nearby."
United States
Greg E.
The price is HK$1,520
HK$3,609 total
includes taxes & fees
11 Jan - 12 Jan 2026
Gold Anchor Cottage - private hot tub getaway!
Indoor pool, outdoor pool, pool loungers
Sea Mist Resort

Aparthotel in Mashpee

Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (144)
"Just there for one night but very enjoyable stay."
United States
Shawna
The price is HK$1,103
HK$1,263 total
includes taxes & fees
29 Dec - 30 Dec
Sea Mist Resort
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

Hampton Inn Cape Cod Canal

Hampton Inn Cape Cod Canal

10/10 Excellent
"Very nicely decorated for the holidays. "
Bernadette 1-night trip
Posted 3 days ago
Hampton Inn Cape Cod Canal

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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Osterville is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Osterville?

With 53 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.