Vacation Rentals with Pool in Lakeside, CT: Compare 10+ Sites & Save

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21 Best Vacation Rentals with Pool in Lakeside (Starting from $225)

Upmarket Country Retreat, Washington, Connecticut
Upmarket Country Retreat, Washington, Connecticut
House
Washington, CT, USA
4.2k from Lakeside center

Parking, Fireplace/Heating, Smoking, Internet, Pool, Oceanfront, View

5 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$670
Average price / night
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2 Hrs NYC, Best Skiing, Shops, Dining,2 Gas Fires,WASHINGTON PoshPadsCT, HotTub
2 Hrs NYC, Best Skiing, Shops, Dining,2 Gas Fires,WASHINGTON PoshPadsCT, HotTub
House
Washington, CT, 06793, United States
2.1k from Lakeside center

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

5 Bedrooms12 Guests
9.4

Superb

12 reviews

$1214
Average price / night
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Historic Colonial Pool Walk to Town
Historic Colonial Pool Walk to Town
House
Litchfield, CT, USA
7.4k from Lakeside center

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

3 Bedrooms6 Guests
New to Booking
$381
Average price / night
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100% WASHINGTON! PoshPadsCT \"SENFF ESTATE\"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ
100% WASHINGTON! PoshPadsCT \"SENFF ESTATE\"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ
House
Washington, CT, 06793, United States
2.3k from Lakeside center

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

8 Bedrooms15 Guests
10.0

Exceptional

16 reviews

$1662
Average price / night
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Litchfield Modern Farmhouse
Litchfield Modern Farmhouse
House
Litchfield, CT, USA
8.6k from Lakeside center

View, Internet, Fireplace/Heating, Sports/Activities, Pool, Air Conditioner, Parking

2 Bedrooms4 Guests
9.1

Superb

6 reviews

$225
Average price / night
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Best Ski Cottage, Restaurants, Shops 2 FPs, 2 Hrs NYC to WASHINGTON! PoshPadsCT
Best Ski Cottage, Restaurants, Shops 2 FPs, 2 Hrs NYC to WASHINGTON! PoshPadsCT
Cottage
Washington, CT, 06793, United States
2.7k from Lakeside center

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

3 Bedrooms8 Guests
9.8

Exceptional

11 reviews

$1121
Average price / night
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ABC Stay - Connecticut Five Bedroom Home
ABC Stay - Connecticut Five Bedroom Home
House
Warren, CT, USA
9.8k from Lakeside center

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

4 Bedrooms10 Guests
New to Booking
$1341
Average price / night
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Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
House
Bethlehem, CT, 06751, United States
2.9k from Lakeside center

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

4 Bedrooms12 Guests
10.0

Exceptional

17 reviews

$620
Average price / night
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Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video
House
Washington, CT, 06793, United States
4.1k from Lakeside center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$579
Average price / night
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2 Hrs NYC, Best Ski Estate, Shopping, Dining WASHINGTON PoshPadsCT \"SUNNY RIDGE\"
2 Hrs NYC, Best Ski Estate, Shopping, Dining WASHINGTON PoshPadsCT \"SUNNY RIDGE\"
House
Washington, CT, 06793, United States
4.5k from Lakeside center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

8 Bedrooms16 Guests
10.0

Exceptional

2 reviews

$1668
Average price / night
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Hilltop House
Hilltop House
House
Litchfield, CT, 06759, United States
5.0k from Lakeside center

Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio, Pool, TV

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$576
Average price / night
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5 bedroom, 14 acre private estate
5 bedroom, 14 acre private estate
House
Bethlehem, CT, 06751, United States
5.0k from Lakeside center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms8 Guests
9.0

Fabulous

7 reviews

$821
Average price / night
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Stunning renovated horse farm with pool, hot tub, and 6 bedrooms.
Stunning renovated horse farm with pool, hot tub, and 6 bedrooms.
House
Morris, CT, 06763, United States
5.5k from Lakeside center

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

6 Bedrooms9 Guests
New to Booking
$1202
Average price / night
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Historic Colonial...Close to Village Green
Historic Colonial...Close to Village Green
House
Litchfield, CT, 06759, United States
7.2k from Lakeside center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$470
Average price / night
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Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
House
Watertown, CT, 06795, United States
7.4k from Lakeside center

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

5 Bedrooms12 Guests
9.6

Exceptional

18 reviews

$1475
Average price / night
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2 Hrs NYC-Best Ski Home, Shopping, Dining, 4Fires, VIEWS! WASHINGTON PoshPadsCT,
2 Hrs NYC-Best Ski Home, Shopping, Dining, 4Fires, VIEWS! WASHINGTON PoshPadsCT,
House
Washington, CT, 06794, United States
7.9k from Lakeside center

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

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1309
Average price / night
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BEST SKI TOWN-WASHINGTON! NYC 2Hrs \"Calhoun5BR\" POSHPADSCT Hot Tub, 4 FPs, Views
BEST SKI TOWN-WASHINGTON! NYC 2Hrs \"Calhoun5BR\" POSHPADSCT Hot Tub, 4 FPs, Views
House
Washington, CT, 06794, United States
8.4k from Lakeside center

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

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1156
Average price / night
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Expansive, Five Bedroom House with Pool.  Ideal for Multiple Family Travel
Expansive, Five Bedroom House with Pool. Ideal for Multiple Family Travel
House
Washington, CT, 06793, United States
8.4k from Lakeside center

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

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1187
Average price / night
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2 Hrs NYC, Best Ski Home, Shopping, Dining, Fire, VIEWS! WASHINGTON PoshPadsCT,
2 Hrs NYC, Best Ski Home, Shopping, Dining, Fire, VIEWS! WASHINGTON PoshPadsCT,
Cottage
Washington Depot, CT, 06794, United States
8.5k from Lakeside center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1108
Average price / night
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Live the good life in this luxury Lake Waramaug retreat!
Live the good life in this luxury Lake Waramaug retreat!
House
New Preston, CT, 06777, United States
8.8k from Lakeside center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

17 reviews

$1964
Average price / night
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House Nestled Bet Vineyards/Pool, Sauna and Spa
House Nestled Bet Vineyards/Pool, Sauna and Spa
House
New Preston, CT, 06777, United States
9.7k from Lakeside center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms10 Guests
9.4

Superb

10 reviews

$1349
Average price / night
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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 Vacation Rentals with Pool in Lakeside.

Stay Near Lakeside's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Lakeside Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 21 verified vacation rentals with a pool in Lakeside. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Lakeside vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $225 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Lakeside offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Lakeside welcome pets. Currently, 15 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Lakeside often include additional outdoor features such as Pool, Fireplace/Heating, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Lakeside offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.