A house by a lake with boats.

Osterville Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Osterville vacation rentals

Private beach nearby, beach bar

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (362 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is AED 1,854
AED 2,121 total
includes taxes & fees
15 Jul - 16 Jul
The Club at New Seabury
Apartment (1 Bedroom) | Interior

3 Mi to Beaches: Peaceful Wareham Getaway

3 Mi to Beaches: Peaceful Wareham Getaway
3.0 star property
Wareham
The price is AED 569
AED 937 total
includes taxes & fees
23 Jul - 24 Jul
3 Mi to Beaches: Peaceful Wareham Getaway
House | 5 bedrooms, desk

Water Access 5-bed 2-bath Retreat

Water Access 5-bed 2-bath Retreat
2.0 star property
Hyannis
Water Access 5-bed 2-bath Retreat
House (3 Bedrooms) | Interior

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
3.0 star property
Sandwich
5 Mi to Beach: Cape Cod Getaway w/ Grill
House | 3 bedrooms, desk

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.5 star property
West Dennis
The price is AED 1,328
AED 2,939 total
includes taxes & fees
13 Jul - 14 Jul
Coastal Haven in West Dennis -15
Cottage (2 Bedrooms) | Interior

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very Good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
Apartment (1 Bedroom) | Interior

Pet-friendly Wareham Retreat Near Onset Beach!

Pet-friendly Wareham Retreat Near Onset Beach!
3.0 star property
Wareham
The price is AED 569
AED 937 total
includes taxes & fees
12 Jul - 13 Jul
Pet-friendly Wareham Retreat Near Onset Beach!
Cottage (2 Bedrooms) | Interior

Walk to Swift's Beach! Classic Cottage w/ Deck

Walk to Swift's Beach! Classic Cottage w/ Deck
3.0 star property
Wareham
10.0 out of 10, Exceptional, (1 review)
"3 of us had a great time in Wareham. The cottage was exactly as advertised and close to many beaches"
United States
Tracy
The price is AED 1,227
AED 2,449 total
includes taxes & fees
8 Aug - 9 Aug
Walk to Swift's Beach! Classic Cottage w/ Deck
Apartment (1 Bedroom) | Interior

3 Mi to Onset Beach & Village! Pet-friendly Apt

3 Mi to Onset Beach & Village! Pet-friendly Apt
3.0 star property
Wareham
3 Mi to Onset Beach & Village! Pet-friendly Apt
Apartment (1 Bedroom) | Interior

3 Mi to Main Street: Newly Renovated Wareham Apt!

3 Mi to Main Street: Newly Renovated Wareham Apt!
3.0 star property
Wareham
The price is AED 569
AED 937 total
includes taxes & fees
23 Jul - 24 Jul
3 Mi to Main Street: Newly Renovated Wareham Apt!
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

All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

8/10 Good
"Property overall was a very nicely maintained, especially the gardens. My biggest complaint was the breakfast or lock of it. Frozen mini bagels, cups size of a dentist rinse cup. Either don’t bother or give people decent breakfast."
Ellen 3-night trip
Posted 1 hour ago
All Seasons Resort, Trademark Collection by Wyndham

Frequently asked questions

Can I find vacation rentals in Osterville?

Yes, we give you a choice of vacation rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more remote option if you'd like a relaxing place to stay.

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

Cape Cod's "Beach Rose": This vacation home rental outside of Osterville offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Osterville?

With 59 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Osterville like?

Vacation rentals are private properties you can book for a short or long stay in Osterville. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.