Estia Villas - Vacation Rentals in Osterville
House
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
505.9 ft²
-
Parking -
Balcony/Terrace -
Internet -
Security/Safety
US $390
/Night
7 Nights - $2,730
House
10.0
(
90 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
3300 ft²
-
Oceanfront -
Parking
-
Ocean View -
Balcony/Terrace
US $1,195
/Night
7 Nights - $8,367
House
9.8
(
45 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
3700 ft²
-
Private Pool -
Oceanfront
-
Parking
-
Pool
US $2,030
/Night
7 Nights - $14,208
House
9.4
(
18 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
2400 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $788
/Night
7 Nights - $5,513
House
10.0
(
26 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2700 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $520
/Night
7 Nights - $3,640
House
10.0
(
20 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $981
/Night
7 Nights - $6,866
House
10.0
(
8 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $530
/Night
7 Nights - $3,713
House
10.0
(
3 Reviews
)
6 Bedrooms
5 Bathrooms
12 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub -
Parking
US $5,068
/Night
7 Nights - $35,476
See More Osterville Vacation Rentals
Luxury Places to Stay in Osterville
Over 158+
Luxury Places to Stay in or Near Osterville
House
10.0
(
2 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $6,401
/Night
7 Nights - $44,809
New
House
6 Bedrooms
7 Bathrooms
22 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $6,045
/Night
7 Nights - $42,316
House
5 Bedrooms
6 Bathrooms
18 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $5,364
/Night
7 Nights - $37,548
House
10.0
(
3 Reviews
)
4 Bedrooms
5 Bathrooms
10 Guests
-
Private Pool
-
Hot Tub
-
Pool
-
Air Conditioner
US $4,681
/Night
7 Nights - $32,768
House
9.4
(
13 Reviews
)
11 Bedrooms
7 Bathrooms
22 Guests
7400 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $3,649
/Night
7 Nights - $25,541
New
House
Waterfront Estate in Prestigious Osterville | Private Beach, Pool & Hot Tub and Central AC-Sleeps 15
9.8
(
6 Reviews
)
6 Bedrooms
5 Bathrooms
15 Guests
4470 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $3,058
/Night
7 Nights - $21,409
House
9.4
(
9 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
3988 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $2,744
/Night
7 Nights - $19,206
House
10.0
(
1 Review
)
6 Bedrooms
7 Bathrooms
12 Guests
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $2,640
/Night
7 Nights - $18,480
See More Osterville Luxury Vacation Rentals
Find More Osterville Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Osterville
Over 34+
Top-Rated Vacation Rentals with a Pool in or Near Osterville
House
9.8
(
36 Reviews
)
7 Bedrooms
7 Bathrooms
10 Guests
7000 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,713
/Night
7 Nights - $11,993
House
9.6
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1344 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $577
/Night
7 Nights - $4,037
House
9.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
10 Guests
1926.74 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $824
/Night
7 Nights - $5,768
House
8.4
(
5 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1930 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $479
/Night
7 Nights - $3,356
House
8.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
8 Guests
1345.49 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
View
US $420
/Night
7 Nights - $2,940
New
House
4 Bedrooms
3 Bathrooms
10 Guests
3015 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,904
/Night
7 Nights - $13,330
New
House
5 Bedrooms
4 Bathrooms
10 Guests
3800 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,658
/Night
7 Nights - $11,605
House
4 Bedrooms
2 Bathrooms
8 Guests
3387 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $630
/Night
7 Nights - $4,412
Pet-Friendly Vacation Rentals in Osterville
Over 44+
Pet-Friendly Vacation Rentals in or Near Osterville
House
1 Bedroom
1 Bathroom
10 Guests
2454.17 ft²
-
Parking
-
View
-
Air Conditioner
-
Internet
US $1,112
/Night
7 Nights - $7,785
House
10.0
(
2 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $755
/Night
7 Nights - $5,288
House
10.0
(
1 Review
)
5 Bedrooms
4 Bathrooms
10 Guests
2450 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,247
/Night
7 Nights - $8,731
House
9.8
(
6 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2900 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,453
/Night
7 Nights - $10,169
House
2 Bedrooms
2 Bathrooms
6 Guests
1671 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $848
/Night
7 Nights - $5,933
House
9.6
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,511
/Night
7 Nights - $10,575
House
10.0
(
2 Reviews
)
4 Bedrooms
3 Bathrooms
11 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $948
/Night
7 Nights - $6,634
House
9.8
(
12 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $507
/Night
7 Nights - $3,549
See More Pet-Friendly Vacation Rentals in Osterville on PetFriendly.io
Large Vacation Homes & Villas in Osterville
Over 29+
Large Vacation Homes & Villas in or Near Osterville
New
House
9.8
(
7 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
2758 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,520
/Night
7 Nights - $10,642
House
10.0
(
2 Reviews
)
6 Bedrooms
5 Bathrooms
15 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,295
/Night
7 Nights - $9,067
House
9.6
(
20 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $697
/Night
7 Nights - $4,882
House
5 Bedrooms
3 Bathrooms
10 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,977
/Night
7 Nights - $13,839
New
House
7 Bedrooms
4 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,921
/Night
7 Nights - $13,445
House
4 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,689
/Night
7 Nights - $11,823
New
House
6 Bedrooms
4 Bathrooms
11 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $1,244
/Night
7 Nights - $8,707
House
10.0
(
6 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $800
/Night
7 Nights - $5,601
See More Family Vacation Rentals in Osterville on FVR
Wheelchair Accessible Vacation Homes in Osterville
Over 1+
Wheelchair Accessible Vacation Homes in or Near Osterville
House
5.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2400 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $450
/Night
7 Nights - $3,150
Osterville Vacation Rentals and Airbnb Places to Stay Under $200
Over 2+
Osterville Vacation Rentals and Airbnb Places to Stay Under $200
New
Apartment
2 Bedrooms
1 Bathroom
4 Guests
796.53 ft²
-
Private Beach -
Oceanfront
-
Breakfast -
Parking
US $126
/Night
7 Nights - $882
Apartment
10.0
(
4 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
764 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $147
/Night
7 Nights - $1,029
See More Osterville Vacation Rental Deals
Instantly Bookable Vacation Homes in Osterville
Over 59+
Instantly Bookable Vacation Homes in or Near Osterville
House
10.0
(
3 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2171 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $451
/Night
7 Nights - $3,160
Cottage
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $545
/Night
7 Nights - $3,816
House
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $475
/Night
7 Nights - $3,322
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Balcony/Terrace
-
Child Friendly -
Laundry -
Barbecue/Outdoor Cooking
US $501
/Night
7 Nights - $3,508
House
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
6 Guests
1288 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $490
/Night
7 Nights - $3,428
House
9.6
(
4 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
TV
US $471
/Night
7 Nights - $3,299
House
9.4
(
13 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1512 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $552
/Night
7 Nights - $3,865
House
9.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1600 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $681
/Night
7 Nights - $4,765
About Osterville Vacation Rentals
With more than 167 Osterville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Osterville.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Osterville, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Osterville. Places to stay near Osterville are 1092.1 ft² on average, with prices averaging US $1,184 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Osterville with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Osterville
| Type | Count |
|---|---|
| Vacation Homes | 157 |
| Cottages | 6 |
| Holiday Apartments | 3 |
Use these Quick Filters to Find a Vacation Rental in Osterville
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osterville.
Weather in Osterville
View the weather forecast for Osterville before booking your Osterville Vacation Rentals to confirm your best time to go.
December - February
High 45°F Low 24°F
March - May
High 66°F Low 27°F
June - August
High 81°F Low 59°F
September - November
High 77°F Low 35°F
Top Attractions Around Osterville, MA
Estiavillas offers a large selection of top attractions around Osterville. Research things to do on your vacation before you visit Osterville.
Stand Up & Paddle Cape Cod
Dowses Beach
Public Beach
Cape Codder Water Park
Harwich Port
Hyannis Harbor
Old Silver Beach
Mayflower Beach
Oak Bluffs Harbor
Inkwell Beach
West Dennis Beach
Seagull Beach
Sandy Neck Beach
Hyannis Port Beach
Falmouth Heights Beach
Katama Beach
Massachusetts Maritime Academy
Woods Hole Ferry Terminal
Water Wizz
Craigville Beach
Other Places to Stay Near Osterville, MA
Osterville Vacation Rental Frequently Asked Questions
How many vacation rentals have private pools in Osterville?
There are 21 vacation rentals with private pools near Osterville. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Osterville are best for families?
If you are looking for a family-friendly vacation home in Osterville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osterville:
How many vacation rentals are available in Osterville?
Currently, the total number of properties listed in 2026 is over 167 in the Osterville area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osterville.
