Search Vacation Homes in Osterville

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In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Osterville vacation homes

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!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
West Brewster
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
$604 nightly
The price is $692
Dec 21 - Dec 22
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
TV, fireplace, foosball, table tennis
The Mermaid Cottage @ The Compound Beach Resort Habitat

The Mermaid Cottage @ The Compound Beach Resort Habitat

The Mermaid Cottage @ The Compound Beach Resort Habitat
Wareham
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.
$562 nightly
The price is $589
Dec 21 - Dec 22
Total with taxes and fees
The Mermaid Cottage @ The Compound Beach Resort Habitat
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

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
$491 nightly
The price is $561
Dec 21 - Dec 22
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Interior
The Park View Room @ The Compound ~E-Bike-Hot Tub-Boats

The Park View Room @ The Compound ~E-Bike-Hot Tub-Boats

The Park View Room @ The Compound ~E-Bike-Hot Tub-Boats
2.0 star property
Wareham
$226 nightly
The price is $229
Dec 21 - Dec 22
Total with taxes and fees
The Park View Room @ The Compound ~E-Bike-Hot Tub-Boats
Pool
Cozy Large Home in Harwich with Patio near Wequassett Resort

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)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
$468 nightly
The price is $518
Dec 21 - Dec 22
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
Property grounds
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

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

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$316 nightly
The price is $350
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Sun loungers, beach towels
Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
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.
$276 nightly
The price is $308
Dec 21 - Dec 22
Total with taxes and fees
Make this charming, modern retreat your home away from home!!
Dining
Big Sandy Beachcomber

Big Sandy Beachcomber

Big Sandy Beachcomber
Ponds of Plymouth
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.
$350 nightly
The price is $391
Dec 22 - Dec 23
Total with taxes and fees
Big Sandy Beachcomber
Smart TV, books
Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District
Sandwich
9.0 out of 10, Wonderful, (17)
"The house was a great cozy place to stay. Ed was pleasant and offer tips on where to go and what to see. We had a great time. "
United States
Justin V.
$356 nightly
The price is $407
Dec 21 - Dec 22
Total with taxes and fees
Oldest Town of Cape Cod In The Historic District
Beach nearby
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
$468 nightly
The price is $518
Dec 21 - Dec 22
Total with taxes and fees
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Smart TV, fireplace
Coastal Haven in West Dennis

Coastal Haven in West Dennis

Coastal Haven in West Dennis
2.0 star property
Dennis
10.0 out of 10, Exceptional, (3)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
United States
Edward R.
$564 nightly
The price is $613
Dec 21 - Dec 22
Total with taxes and fees
Coastal Haven in West Dennis
Smart TV, fireplace, books
Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod
South Yarmouth
10.0 out of 10, Exceptional, (12)
"Great stay!"
United States
Kevin B.
$487 nightly
The price is $557
Jan 3 - Jan 4, 2026
Total with taxes and fees
Modern Beach & Pond Getaway; Heart of Cape Cod
Beach
Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC

Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC

Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC
2.0 star property
Dennis Port
$410 nightly
The price is $469
Dec 21 - Dec 22
Total with taxes and fees
Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC
Terrace/patio
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (129)
"Very clean and nice place for two for a quick peaceful stay. Great location."
United States
Michele G.
$343 nightly
The price is $383
Dec 21 - Dec 22
Total with taxes and fees
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Smart TV
Gold Anchor Cottage - private hot tub getaway!

Gold Anchor Cottage - private hot tub getaway!

Gold Anchor Cottage - private hot tub getaway!
Sandwich
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.
$386 nightly
The price is $442
Jan 11 - Jan 12, 2026
Total with taxes and fees
Gold Anchor Cottage - private hot tub getaway!
Beach nearby, sun loungers, beach towels
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.
Wareham
10.0 out of 10, Exceptional, (5)
"This property is just as described, even better in person. Very cute and clean, with everything you could possibly need during your stay. Great location and very quiet neighborhood. Definitely recommend. "
United States
Dayna F.
$461 nightly
The price is $514
Dec 22 - Dec 23
Total with taxes and fees
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.
Exterior
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
$273 nightly
The price is $313
Dec 28 - Dec 29
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Property grounds
3BR, central air, washer & dryer, grill, near ocean beaches & freshwater ponds

3BR, central air, washer & dryer, grill, near ocean beaches & freshwater ponds

3BR, central air, washer & dryer, grill, near ocean beaches & freshwater ponds
Harwich
10.0 out of 10, Exceptional, (13)
"Lovely, well-maintained home! Everything in the house was clean, organized, and labeled. The hosts were excellent communicators and responded efficiently when we had questions. Exactly what our family was looking for during our stay on the Cape. "
United States
Melissa V.
$508 nightly
The price is $581
Dec 21 - Dec 22
Total with taxes and fees
3BR, central air, washer & dryer, grill, near ocean beaches & freshwater ponds
Fridge, microwave, oven, stovetop
Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!

Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!

Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!
Yarmouth
10.0 out of 10, Exceptional, (13)
"We rented this house for a family vacation and would without a doubt rent it again! Everything you can possibly need was at the house. If you needed anything additional the host was very responsive and there to assist. We loved the time we got to spend here together. "
United States
Cara B.
$628 nightly
The price is $695
Jan 5 - Jan 6, 2026
Total with taxes and fees
Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!
Interior
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (211)
"We had a great stay. House is spacious, clean and well-stocked with everything we needed. We loved that we were able to walk to downtown shops and restaurants, the ferry to Martha’s Vineyard and the beach. Would definitely stay here again. "
United States
Ava B.
$432 nightly
The price is $494
Dec 21 - Dec 22
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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

Courtyard Resort

Courtyard Resort

10/10 Excellent
"Clean rooms, full kitchens, good area. "
Michael 1-night trip
Posted 3 days ago
Courtyard Resort

Find out more about Osterville

Osterville Vacation Homes information

Number of reviews
654
Accommodation
2896 Vacation Homes
Lowest Price
$229
Highest Price
$695

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