Family-Friendly Vacation Rentals in Watch Hill Historic District, RI: Compare 10+ Sites & Save

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  3.  USA

  4.  Rhode Island

  5.  Westerly
  6.  Watch Hill Historic District

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112 Best Family Vacation Rentals in Watch Hill Historic District (Starting from $145)

Walk to Pawcatuck River Family-Friendly Home!
Walk to Pawcatuck River Family-Friendly Home!
House
Pawcatuck, CT, USA
4.5k from Watch Hill Historic District center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms4 Guests
New to Booking
$348
Average price / night
Check Availability
The Saltbox - Watch Hill's Award-Winning Waterfront Retreat.
The Saltbox - Watch Hill's Award-Winning Waterfront Retreat.
Condo
Westerly, RI, 02891, United States
0.1k from Watch Hill Historic District center

Balcony, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$1660
Average price / night
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The Captains Perch
The Captains Perch
Apartment
Stonington, CT, USA
4.7k from Watch Hill Historic District center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$317
Average price / night
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Charming 4-bedroom cottage Steps From East Beach
Charming 4-bedroom cottage Steps From East Beach
Cottage
Westerly, RI, 02891, United States
1.5k from Watch Hill Historic District center

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

4 Bedrooms8 Guests
New to Booking
$3534
Average price / night
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Harbor House on Main Historic 5BR Retreat Near Downtown Mystic
Harbor House on Main Historic 5BR Retreat Near Downtown Mystic
House
Stonington, CT, USA
5.1k from Watch Hill Historic District center

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

5 Bedrooms12 Guests
New to Booking
$459
Average price / night
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BRAND New 4 BED Luxurious Villa Ocean Views with NEW private pool.
BRAND New 4 BED Luxurious Villa Ocean Views with NEW private pool.
Villa
Westerly, RI, 02891, United States
2.7k from Watch Hill Historic District center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms12 Guests
10.0

Exceptional

11 reviews

$1615
Average price / night
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The Seafarers Stay A Nautically Themed 3BR Flat in Stonington Borough
The Seafarers Stay A Nautically Themed 3BR Flat in Stonington Borough
Apartment
Stonington, CT, USA
5.1k from Watch Hill Historic District center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
New to Booking
$276
Average price / night
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\"The Boulders\" - A Watch Hill Five Bedroom House
\"The Boulders\" - A Watch Hill Five Bedroom House
House
Westerly, RI, 02891, United States
3.3k from Watch Hill Historic District center

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

5 Bedrooms12 Guests
10.0

Exceptional

47 reviews

$1288
Average price / night
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Whalers Rest A Bright and Historic 2BR Flat in Stonington Borough
Whalers Rest A Bright and Historic 2BR Flat in Stonington Borough
Apartment
Stonington, CT, USA
5.1k from Watch Hill Historic District center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

5 Bedrooms5 Guests
New to Booking
$238
Average price / night
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Fabulous waterfront property, 3 bed/3 bath, walk to beach.
Fabulous waterfront property, 3 bed/3 bath, walk to beach.
House
Westerly, RI, 02891, United States
3.4k from Watch Hill Historic District center

Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1465
Average price / night
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37 Wamphassuc Rd Chteau Stonington
37 Wamphassuc Rd Chteau Stonington
House
Stonington, CT, USA
6.4k from Watch Hill Historic District center

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

1 Bedroom8 Guests
9.8

Exceptional

6 reviews

$656
Average price / night
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Quintessential New England Home on Private Beach
Quintessential New England Home on Private Beach
House
Westerly, RI, 02891, United States
3.5k from Watch Hill Historic District center

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

4 Bedrooms10 Guests
10.0

Exceptional

30 reviews

$1539
Average price / night
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Cozy Chateau
Cozy Chateau
House
Stonington, CT, USA
6.4k from Watch Hill Historic District center

Security/Safety, Air Conditioner, Balcony/Terrace, View, Internet, Parking, Child Friendly

1 Bedroom3 Guests
New to Booking
$288
Average price / night
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Ocean Shire Coastal Retreat and Beach Pass
Ocean Shire Coastal Retreat and Beach Pass
Cottage
Westerly, RI, 02891, United States
4.1k from Watch Hill Historic District center

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

2 Bedrooms5 Guests
New to Booking
$487
Average price / night
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Westerly Apt Steps From Downtown and Beaches Nearby
Westerly Apt Steps From Downtown and Beaches Nearby
Apartment
Westerly, RI, USA
6.6k from Watch Hill Historic District center

Guest Services, Fireplace/Heating, Parking, Accessibility, Security/Safety, Internet, Child Friendly

3 Bedrooms5 Guests
New to Booking
$341
Average price / night
Check Availability
Elegant Waterfront Estate On 2 Acres ~ Private Pool ~ 12 min from Mystic!
Elegant Waterfront Estate On 2 Acres ~ Private Pool ~ 12 min from Mystic!
House
Stonington, CT, 06379, United States
4.1k from Watch Hill Historic District center

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

5 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$1374
Average price / night
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Rest in Westerly
Rest in Westerly
House
Westerly, RI, USA
7.0k from Watch Hill Historic District center

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

3 Bedrooms6 Guests
9.9

Exceptional

12 reviews

$493
Average price / night
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Modern Beach House Serenity
Modern Beach House Serenity
House
Westerly, RI, 02891, United States
4.3k from Watch Hill Historic District center

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

3 Bedrooms8 Guests
9.8

Exceptional

7 reviews

$751
Average price / night
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5 Mi to Beaches Historic Apartment in Westerly!
5 Mi to Beaches Historic Apartment in Westerly!
Apartment
Westerly, RI, USA
7.5k from Watch Hill Historic District center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
7.0

Good

1 reviews

$239
Average price / night
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Amazing Ocean Front 2 Story Home, Steps Away From The Water
Amazing Ocean Front 2 Story Home, Steps Away From The Water
House
Westerly, RI, 02891, United States
4.4k from Watch Hill Historic District center

AC, Balcony, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms8 Guests
9.8

Exceptional

108 reviews

$598
Average price / night
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Cozy, cute beach condo in Westerly RI . Best value in Westerly!
Cozy, cute beach condo in Westerly RI . Best value in Westerly!
Apartment
Westerly, RI, USA
8.4k from Watch Hill Historic District center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering, Condos

1 Bedroom3 Guests
7.5

Good

2 reviews

$145
Average price / night
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5 STAR Coastal Farmhouse- Dog Friendly- 3BR in Westerly! Minutes to Beach & Town
5 STAR Coastal Farmhouse- Dog Friendly- 3BR in Westerly! Minutes to Beach & Town
House
Westerly, RI, 02891, United States
4.5k from Watch Hill Historic District center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.4

Superb

18 reviews

$644
Average price / night
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Escape to coastal bliss in this charming condo in Westerly—your perfect getaway!
Escape to coastal bliss in this charming condo in Westerly—your perfect getaway!
Condo
Westerly, RI, 02891, United States
4.5k from Watch Hill Historic District center

AC, Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$251
Average price / night
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Water View 3BR Cottage in Stonington Borough + Walk to Village
Water View 3BR Cottage in Stonington Borough + Walk to Village
Cottage
Stonington, CT, 06378, United States
4.6k from Watch Hill Historic District center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$536
Average price / night
Check Availability
Waterfront Pool Cottage Watch Hill Misquamicut Westerly Beaches
Waterfront Pool Cottage Watch Hill Misquamicut Westerly Beaches
Cottage
Westerly, RI, 02891, United States
4.6k from Watch Hill Historic District center

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

2 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$1070
Average price / night
Check Availability
Stonington Borough  2 bed, 2 bath, Sleeps 6, close to beach, Fire place, pets
Stonington Borough 2 bed, 2 bath, Sleeps 6, close to beach, Fire place, pets
House
Stonington, CT, 06378, United States
4.6k from Watch Hill Historic District center

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

3 Bedrooms6 Guests
10.0

Exceptional

74 reviews

$573
Average price / night
Check Availability
Private Sanctuary in Stonington Boro - Stunning Coastal Views - Boaters Paradise
Private Sanctuary in Stonington Boro - Stunning Coastal Views - Boaters Paradise
House
Stonington, CT, 06378, United States
4.6k from Watch Hill Historic District center

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

3 Bedrooms6 Guests
9.8

Exceptional

46 reviews

$799
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 Family Vacation Rentals in Watch Hill Historic District.

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Watch Hill Historic District Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 112 verified family-friendly vacation rentals in Watch Hill Historic District. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Watch Hill Historic District vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $145 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Watch Hill Historic District offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Watch Hill Historic District are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Watch Hill Historic District often include amenities such as Child Friendly, Fireplace/Heating, and View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.