Osterville Vacation Rentals

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Vacation Rentals in Osterville

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (349)
"Very nice place to stay "
The price is CA $224
CA $257 total
includes taxes & fees
Sep 29 - Sep 30
Holly Tree Resort

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (313)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The price is CA $291
CA $365 total
includes taxes & fees
Sep 4 - Sep 5
The Cove at Yarmouth by VRI Americas

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (283)
"All around a great place to stay!"
The price is CA $328
CA $376 total
includes taxes & fees
Sep 30 - Oct 1
Edgewater Beach Resort, a VRI resort

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (327)
"Nice amenities. "
The price is CA $336
CA $385 total
includes taxes & fees
Sep 2 - Sep 3
The Club at New Seabury

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (107)
"I only stayed for a night, but I found the property comfortable and quiet and I enjoyed the hot tub."
The price is CA $301
CA $344 total
includes taxes & fees
Sep 28 - Sep 29
Brewster Green Resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (162)
"Overall everything was great. Rooms are clean. Very quiet. The upper outside deck requires repair but my understanding is owners association is aware and addressing. I think its our fourth time there. Keep going back. Only thing is we wished there was an outdoor pool. Would be great on those warm sunny days."
The price is CA $230
CA $264 total
includes taxes & fees
Sep 14 - Sep 15
Riverview Resort

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

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (127)
"Nice home, great views and very relaxing stay."
Steps to the beach with an ocean view,

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (134)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is CA $197
CA $225 total
includes taxes & fees
Sep 30 - Oct 1
Sea Mist Resort

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (219)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

*Oceanfront Beach Home*

10.0 out of 10, Exceptional, (80)
"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*

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

Stunning Oceanfront Home With Amazing Views ~ Private Beach

9.6 out of 10, Exceptional, (112)
"This property was as advertised. Right on a private beach, the views here are incredible. Make sure you plan to see a sunrise or sunset! Owner is very easy to work with and responsive. "
The price is CA $1,235
CA $2,112 total
includes taxes & fees
Sep 21 - Sep 22
Stunning Oceanfront Home With Amazing Views ~ Private Beach

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is CA $110
CA $244 total
includes taxes & fees
Sep 3 - Sep 4
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (164)
"Recommended "
The price is CA $123
CA $430 total
includes taxes & fees
Sep 1 - Sep 2
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

6.4 out of 10, (26)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Mermaid Cottage! beautiful propety!

10.0 out of 10, Exceptional, (102)
"Great property and location!"
Mermaid Cottage! beautiful propety!

Peaceful Cozy Water Front Cottage. Step back in time and ENJOY

9.6 out of 10, Exceptional, (50)
"My boyfriend and I had the pleasure of staying in this wonderful place surrounded by nature! The view is amazing at all times! Everywhere you look! The sound of nature and the animals together with the view was perfect! Thank you so much Matt and Karen! "
Peaceful Cozy Water Front Cottage. Step back in time and ENJOY

Cape Cod Bay Home w/ Deck + Private Beach Access

9.6 out of 10, Exceptional, (33)
"Enjoyed the location and the house very much"
Cape Cod Bay Home w/ Deck + Private Beach Access
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

Find out more about Osterville

Find out more about Osterville

Everything you need to know about Osterville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osterville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osterville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osterville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osterville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osterville vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osterville vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osterville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osterville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osterville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill: This vacation home rental outside of Osterville offers a balcony, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Osterville?

With 75 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.