Osterville Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in Osterville

Holly Tree Resort
Front of property

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (356)
"Nice rooms nice property great location"
Holly Tree Resort
Edgewater Beach Resort, a VRI resort
BBQ/picnic Area

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (286)
"All around a great place to stay!"
The price is HK$1,675
HK$1,916 total
includes taxes & fees
23 Oct - 24 Oct
Edgewater Beach Resort, a VRI resort
Brewster Green Resort
Indoor pool, outdoor pool

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (112)
"Great centralized location for all of our travel destinations. Nantucket, Martha’s Vineyard, Hyannis, Chatham and Provincetown. Very clean and spacious accommodations. Highly recommend for families with small children. "
The price is HK$1,502
HK$1,720 total
includes taxes & fees
5 Oct - 6 Oct
Brewster Green Resort
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (336)
"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 "
The Club at New Seabury
Riverview Resort
Sun deck

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (163)
"The hotel could use some upgrades/updates "
The price is HK$1,552
HK$1,776 total
includes taxes & fees
22 Oct - 23 Oct
Riverview Resort
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (181)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters
The Cove at Yarmouth by VRI Americas
Aerial view

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (318)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The Cove at Yarmouth by VRI Americas
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel cot

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
The price is HK$4,864
HK$10,376 total
includes taxes & fees
27 Oct - 28 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Sea Mist Resort
Indoor pool, outdoor pool, pool loungers

Sea Mist Resort

3.0 star property
8.6 out of 10, Excellent, (136)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is HK$1,847
HK$2,114 total
includes taxes & fees
24 Oct - 25 Oct
Sea Mist Resort
Steps to the beach with an ocean view,
On the beach, sun-loungers, beach towels

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (132)
"Great stay."
Steps to the beach with an ocean view,
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun-loungers

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (226)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!
*Oceanfront Beach Home*
On the beach, sun-loungers, beach towels

*Oceanfront Beach Home*

10.0 out of 10, Exceptional, (82)
"Salt Eire was a lovely, cozy home. The beach views were phenomenal. The gas fireplace was perfect for a winter visit! The hosts supplied everything we could possibly need. It was a wonderful weekend getaway. "
*Oceanfront Beach Home*
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Smart TV

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is HK$2,335
HK$4,172 total
includes taxes & fees
1 Nov - 2 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Cape Cod Bay Home w/ Deck + Private Beach Access
On the beach

Cape Cod Bay Home w/ Deck + Private Beach Access

9.6 out of 10, Exceptional, (34)
"Stunning house! Beautifully appointed"
Cape Cod Bay Home w/ Deck + Private Beach Access
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.4 out of 10, Exceptional, (91)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is HK$2,101
HK$3,877 total
includes taxes & fees
8 Oct - 9 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]
Interior

Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]

9.6 out of 10, Exceptional, (136)
"Great location by the beach. We loved staying here!"
The price is HK$2,638
HK$4,676 total
includes taxes & fees
13 Oct - 14 Oct
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]
Steps to a private beach in a classic Cape cottage. Pet-friendly!
On the beach, sun-loungers, beach towels

Steps to a private beach in a classic Cape cottage. Pet-friendly!

8.8 out of 10, Excellent, (26)
"Quaint, quiet on the off season, great outdoor shower with plenty of hot water! Perfect beach getaway! "
Steps to a private beach in a classic Cape cottage. Pet-friendly!
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Exterior

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

10.0 out of 10, Exceptional, (111)
"Great outdoor spaces. Loved the kayaks, beach and fire pit. Our 2 year old grandson loved the outdoor shower. Our dog had a ball chasing squirrels in the fenced backyard. We would definitely stay again. Close to everything in Falmouth including Woodneck beach, our low tide favorite. "
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Cape Cod Estate: 2 Homes, Pool, Tennis Court, Game Barn and Bar, Sleeps 20
Outdoor pool, a heated pool

Cape Cod Estate: 2 Homes, Pool, Tennis Court, Game Barn and Bar, Sleeps 20

2.0 star property
10.0 out of 10, Exceptional, (9)
"This is such a wonderful property! Our group of 13 had plenty of space to hang out all together and also room to spread out. The owners are fantastic as well. We couldn't have asked for a better home away from home for our first trip to the Cape. Thank you!"
Cape Cod Estate: 2 Homes, Pool, Tennis Court, Game Barn and Bar, Sleeps 20
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

10/10 Excellent
"It was what one would expect!!!"
James 1-night trip
Posted 3 days ago
Margaritaville Resort Cape Cod

Find out more about Osterville

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 70 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?

Dowses Beach and Public Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Stand Up & Paddle Cape Cod. Main Street and Craigville Beach 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.