Short-Term Rentals in Lakeside, CT: Compare 10+ Sites & Save

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80 Best Short-Term Rentals in Lakeside (Starting from $134)

Waterfront Home on Bantam Lake with Private Beach
Waterfront Home on Bantam Lake with Private Beach
House
Morris, CT, USA
1.8k from Lakeside center

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

3 Bedrooms7 Guests
10.0

Exceptional

4 reviews

$650
Average price / night
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Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway
Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway
House
Morris, CT, 06763, United States
1.8k from Lakeside center

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

3 Bedrooms7 Guests
9.8

Exceptional

44 reviews

$487
Average price / night
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Spectacular Cottage at Bantam Lake, Sleeps 12
Spectacular Cottage at Bantam Lake, Sleeps 12
House
Morris, CT, USA
2.9k from Lakeside center

Air Conditioner, Internet, Parking, Child Friendly

8 Bedrooms12 Guests
New to Booking
$625
Average price / night
Check Availability
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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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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Bright and Sunny Direct Waterfront with Private Sandy Beach -
Bright and Sunny Direct Waterfront with Private Sandy Beach -
House
Morris, CT, 06763, United States
2.2k from Lakeside center

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

3 Bedrooms10 Guests
10.0

Exceptional

35 reviews

$622
Average price / night
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Connecticut Retreat Steps to Historic Downtown!
Connecticut Retreat Steps to Historic Downtown!
House
Litchfield, CT, USA
4.8k from Lakeside center

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

2 Bedrooms4 Guests
8.5

Very Good

6 reviews

$134
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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Walk to Memorial Park Pet-Friendly Bethlehem Home
Walk to Memorial Park Pet-Friendly Bethlehem Home
Apartment
Bethlehem, CT, USA
5.6k from Lakeside center

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

1 Bedroom2 Guests
9.5

Superb

2 reviews

$138
Average price / night
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Cozy 2-bedroom Cottage with Access to Bantam Lake
Cozy 2-bedroom Cottage with Access to Bantam Lake
Cottage
Morris, CT, 06763, United States
2.4k from Lakeside center

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

2 Bedrooms6 Guests
9.6

Exceptional

18 reviews

$423
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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Escape to Bantam Lake. Waterfront!
Escape to Bantam Lake. Waterfront!
Cottage
Morris, CT, 06763, United States
2.5k from Lakeside center

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

2 Bedrooms6 Guests
New to Booking
$420
Average price / night
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Cozy Litchfield House with Fenced-In Yard and Fire Pit
Cozy Litchfield House with Fenced-In Yard and Fire Pit
House
Litchfield, CT, USA
7.7k from Lakeside center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$250
Average price / night
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3 Lake Cottages, Waterfront for 25 Guests
3 Lake Cottages, Waterfront for 25 Guests
House
Morris, CT, 06763, United States
2.5k from Lakeside center

13 Bedrooms16 Guests
New to Booking
$1996
Average price / night
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Tranquil setting in the hills of Litchfield
Tranquil setting in the hills of Litchfield
Apartment
Bethlehem, CT, USA
8.4k from Lakeside center

Internet, Pet Friendly, Parking, Air Conditioner, Child Friendly

3 Bedrooms8 Guests
New to Booking
$158
Average price / night
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Bantam Lake Cottage - 4 min walk to lake/shared beach, 6 Kayaks, 2 SUP, fire pit
Bantam Lake Cottage - 4 min walk to lake/shared beach, 6 Kayaks, 2 SUP, fire pit
Cottage
Morris, CT, 06763, United States
2.5k from Lakeside center

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

2 Bedrooms6 Guests
10.0

Exceptional

34 reviews

$361
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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Viewpoint Cottage with Dock, Kayaks
Viewpoint Cottage with Dock, Kayaks
House
Morris, CT, 06763, United States
2.6k from Lakeside center

AC, Balcony, Fireplace, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms7 Guests
New to Booking
$460
Average price / night
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Nature's Nest - Woodland Retreat - Fireplace - Quiet and Cozy
Nature's Nest - Woodland Retreat - Fireplace - Quiet and Cozy
House
Bethlehem, CT, USA
8.7k from Lakeside center

Security/Safety, Parking, Laundry, Internet, Barbecue/Outdoor Cooking, Air Conditioner, Balcony/Terrace

1 Bedroom7 Guests
New to Booking
$370
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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Stunning Warren Lakefront Home Deck, Grill, Sauna
Stunning Warren Lakefront Home Deck, Grill, Sauna
House
Warren, CT, USA
8.9k from Lakeside center

Fireplace/Heating, Pet Friendly, Oceanfront, Guest Services, Accessibility, Ocean View, View

7 Bedrooms19 Guests
New to Booking
$2825
Average price / night
Check Availability
Experience Perch Rocks!  A Unique Private Waterfront Cottage on Bantam Lake
Experience Perch Rocks! A Unique Private Waterfront Cottage on Bantam Lake
Cottage
Morris, CT, 06763, United States
2.8k from Lakeside center

Barbecue, Fireplace, Free Parking, Kitchen, No Smoking, Outdoor Space, Patio, TV

2 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$1023
Average price / night
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Dainty New Preston Cottage with Dock and Lake Views!
Dainty New Preston Cottage with Dock and Lake Views!
House
New Preston, CT, USA
9.7k from Lakeside center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms4 Guests
9.5

Superb

2 reviews

$236
Average price / night
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Lakefront Cottage w/Dock, Kayaks
Lakefront Cottage w/Dock, Kayaks
House
Morris, CT, 06763, United States
2.9k from Lakeside center

3 Bedrooms6 Guests
New to Booking
$425
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
Check Availability
Waterfront modern oasis under 2 hours from NYC. Lots to enjoy all year long!
Waterfront modern oasis under 2 hours from NYC. Lots to enjoy all year long!
Cottage
Bethlehem, CT, 06751, United States
3.5k from Lakeside center

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

2 Bedrooms4 Guests
10.0

Exceptional

15 reviews

$396
Average price / night
Check Availability
Lakefront Charming Cottage Retreat, Bethlehem CT
Lakefront Charming Cottage Retreat, Bethlehem CT
Cottage
Bethlehem, CT, 06751, United States
3.6k from Lakeside center

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

2 Bedrooms5 Guests
9.8

Exceptional

6 reviews

$364
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 Short-Term Rentals 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 Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 80 verified short-term rentals in Lakeside, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Lakeside vary depending on location, property size, and travel dates. Rates typically start from around $134 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Lakeside include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Lakeside, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Lakeside often include amenities such as Fireplace/Heating, Internet, and Child Friendly, providing a comfortable and convenient stay.

Short-term rentals in Lakeside are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.