Oceanfront Rentals in Sheep Pond, MA: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  Massachusetts

  5.  Brewster
  6.  Sheep Pond

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921 Best Oceanfront Rentals in Sheep Pond (Starting from $266)

Family Lakeside Escape with Private Beach and Calm Waters
Family Lakeside Escape with Private Beach and Calm Waters
House
Harwich, MA, USA
2.5k from Sheep Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$405
Average price / night
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Long Pond Lux Estate. Pickleball, Private Dock, Private Beach Access
Long Pond Lux Estate. Pickleball, Private Dock, Private Beach Access
House
Brewster, MA, 02631, United States
0.5k from Sheep Pond center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms16 Guests
10.0

Exceptional

34 reviews

$2681
Average price / night
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Peaceful Retreat on Chilton Lane
Peaceful Retreat on Chilton Lane
House
Brewster, MA, USA
2.5k from Sheep Pond center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

2 Bedrooms5 Guests
New to Booking
$508
Average price / night
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Pond front with Private Beach and Central A/C
Pond front with Private Beach and Central A/C
House
Brewster, MA, 02631-2555, United States
0.6k from Sheep Pond center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$427
Average price / night
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The Brewster Pearl
The Brewster Pearl
House
Brewster, MA, USA
2.8k from Sheep Pond center

Oceanfront, Air Conditioner, Ocean View, Internet, View, Barbecue/Outdoor Cooking, Guest Services

1 Bedroom8 Guests
New to Booking
$350
Average price / night
Check Availability
5 Bedrooms | Water Views | Private Pond Beach | Outdoor Shower
5 Bedrooms | Water Views | Private Pond Beach | Outdoor Shower
House
Brewster, MA, 02631, United States
0.6k from Sheep Pond center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$599
Average price / night
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Cape Cod Villa
Cape Cod Villa
Villa
Harwich, MA, USA
3.6k from Sheep Pond center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
9.9

Exceptional

13 reviews

$574
Average price / night
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Beautiful Home Close to Ponds and Beach!
Beautiful Home Close to Ponds and Beach!
House
Brewster, MA, 02631, United States
0.7k from Sheep Pond center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.8

Exceptional

13 reviews

$470
Average price / night
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The Mansion at Ocean Edge Resort & Golf Club
The Mansion at Ocean Edge Resort & Golf Club
Resort
Brewster, MA, USA
4.0k from Sheep Pond center

Luxury, Accommodations, Pools, Resorts, Parking, Spa, 5-star, Lodgings, Beach

70 Bedrooms22 Guests
8.5

Very Good

80 reviews

$790
Average price / night
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Short walk to Sheep Pond Private Beach!
Short walk to Sheep Pond Private Beach!
House
Brewster, MA, 02631, United States
0.9k from Sheep Pond center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$372
Average price / night
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Cape Cod heated Pool, Putting Green, Speak Easy, Game room,
Cape Cod heated Pool, Putting Green, Speak Easy, Game room,
House
Harwich, MA, USA
4.0k from Sheep Pond center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$743
Average price / night
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Cozy family retreat with kayaks, board games, AC, and beach access
Cozy family retreat with kayaks, board games, AC, and beach access
House
Brewster, MA, 02631, United States
1.1k from Sheep Pond center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$861
Average price / night
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The Villages at Ocean Edge Resort & Golf Club
The Villages at Ocean Edge Resort & Golf Club
Resort
MA, USA
4.1k from Sheep Pond center

Accommodations, Pools, Resorts, Parking, Spa, Golf, Romantic, 3-star, Lodgings

247 Bedrooms51 Guests
8.5

Very Good

280 reviews

$364
Average price / night
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Steps to Freshwater Beach Kayaks Sauna!
Steps to Freshwater Beach Kayaks Sauna!
House
Brewster, MA, 02631, United States
1.1k from Sheep Pond center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

5 Bedrooms11 Guests
9.8

Exceptional

12 reviews

$1015
Average price / night
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Walk to Private Bayside Beach
Walk to Private Bayside Beach
House
Brewster, MA, USA
4.2k from Sheep Pond center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms6 Guests
New to Booking
$312
Average price / night
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Sandy Hill Cottage- Newly renovated beach retreat, perfect for families
Sandy Hill Cottage- Newly renovated beach retreat, perfect for families
House
Brewster, MA, 02631, United States
1.6k from Sheep Pond center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

40 reviews

$515
Average price / night
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Rainbow Cottage
Rainbow Cottage
House
Brewster, MA, USA
4.3k from Sheep Pond center

Internet, Air Conditioner, Oceanfront, Ocean View, Parking, Private Beach, View

2 Bedrooms4 Guests
New to Booking
$563
Average price / night
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Hot Tub 1 Mile to Swimming on Long Pond!
Hot Tub 1 Mile to Swimming on Long Pond!
House
Brewster, MA, 02631, United States
1.6k from Sheep Pond center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.6

Exceptional

18 reviews

$595
Average price / night
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Cape Landing Cottage
Cape Landing Cottage
House
Brewster, MA, USA
5.3k from Sheep Pond center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$660
Average price / night
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Two bedroom condo in Ocean Edge with central air
Two bedroom condo in Ocean Edge with central air
Condo
Brewster, MA, 02631, United States
1.7k from Sheep Pond center

AC, Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

11 reviews

$359
Average price / night
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Lakefront - Long Pond, Brewster: On the water, kayak, swim, fish, relax!
Lakefront - Long Pond, Brewster: On the water, kayak, swim, fish, relax!
House
Brewster, MA, 02631, United States
1.7k from Sheep Pond center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.0

Fabulous

15 reviews

$519
Average price / night
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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
House
Brewster, MA, 02631, United States
1.7k from Sheep Pond center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms9 Guests
9.6

Exceptional

51 reviews

$590
Average price / night
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Cape Cod Getaway - near Seymour Pond and Rail Trail; Bay Beaches w/in a few mile
Cape Cod Getaway - near Seymour Pond and Rail Trail; Bay Beaches w/in a few mile
House
Brewster, MA, 02631, United States
1.8k from Sheep Pond center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$619
Average price / night
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Walk to Beach, AC, WiFi, walk to bike path
Walk to Beach, AC, WiFi, walk to bike path
House
Brewster, MA, 02631, United States
1.8k from Sheep Pond center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.6

Exceptional

7 reviews

$426
Average price / night
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Lovely home w/free WiFi/spacious patio/spiral staircase - near shops/restaurants
Lovely home w/free WiFi/spacious patio/spiral staircase - near shops/restaurants
House
Brewster, MA, 02631, United States
1.8k from Sheep Pond center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Kitchen, Laundry

1 Bedroom6 Guests
8.8

Fabulous

21 reviews

$564
Average price / night
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Brewster 3 Bedroom getaway with plenty of green space!
Brewster 3 Bedroom getaway with plenty of green space!
House
Brewster, MA, 02631, United States
1.8k from Sheep Pond center

AC, Arcade, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms8 Guests
8.8

Fabulous

8 reviews

$354
Average price / night
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Shop, Swim, Hike, Bike in Historic Brewster MA!
Shop, Swim, Hike, Bike in Historic Brewster MA!
House
Brewster, MA, 02613, United States
1.8k from Sheep Pond center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
9.8

Exceptional

35 reviews

$266
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Sheep Pond.

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Sheep Pond Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 921 verified oceanfront rentals in Sheep Pond. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Sheep Pond vary depending on the property size, exact beachfront location, and season. Rates typically start from around $266 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Sheep Pond offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Sheep Pond welcome pets. Currently, 36 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Sheep Pond often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.