Lakeside Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Lakeside, Connecticut, USA

Waterfront Home on Bantam Lake with Private Beach
10.0 (6 Reviews)
3 Bedrooms 7 Guests
Upmarket Country Retreat Washington Connecticut
10.0 (1 Review)
5 Bedrooms 6 Guests
Escape to Bantam Lake. Waterfront!
10.0 (4 Reviews)
2 Bedrooms 6 Guests
Connecticut Retreat: Steps to Historic Downtown!
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8.5 (8 Reviews)
2 Bedrooms 4 Guests
Quaint cottage located directly on Long Meadow Pond
9.8 (104 Reviews)
2 Bedrooms 6 Guests
Beach, Paddle Boards. Swim
9.8 (47 Reviews)
2 Bedrooms 4 Guests
Connecticut Retreat: Steps to Historic Downtown!
9.8 (25 Reviews)
2 Bedrooms 4 Guests
Bright and Sunny Direct Waterfront with Private Sandy Beach -
10.0 (35 Reviews)
3 Bedrooms 10 Guests
NEW Modern Estate, Pool, Theater + Peloton
10.0 (22 Reviews)
4 Bedrooms 8 Guests
Bantam Beauty - Surrounded By Nature!
10.0 (21 Reviews)
5 Bedrooms 10 Guests
Hilltop House
FromCA $1,011 per night
10.0 (10 Reviews)
3 Bedrooms 6 Guests
Bespoke Litchfield - Family Friendly, Hot Tub
10.0 (2 Reviews)
5 Bedrooms 14 Guests
Upmarket Country Retreat, Washington, Connecticut
10.0 (1 Review)
5 Bedrooms 8 Guests
Charming lakeside cottage and guest cottage with spectacular views
9.8 (19 Reviews)
5 Bedrooms 10 Guests
3 Lake Cottages, Waterfront for 25 Guests
New
13 Bedrooms 16 Guests
Spectacular Cottage at Bantam Lake, Sleeps 12
New
7 Bedrooms 12 Guests
Viewpoint Cottage with Dock, Kayaks
New
3 Bedrooms 7 Guests
Lakefront Cottage w/Dock, Kayaks
New
3 Bedrooms 6 Guests
Bantam Lake Loft Retreat!
FromCA $881 per night
New
3 Bedrooms 6 Guests
Lakefront Charming Cottage Retreat
9.8 (6 Reviews)
2 Bedrooms 5 Guests
Cozy 2-bedroom Cottage with Access to Bantam Lake
9.6 (18 Reviews)
2 Bedrooms 6 Guests
Super comfy, chic converted barn with saltwater pool on 6 acres.
10.0 (25 Reviews)
3 Bedrooms 8 Guests
Jim & Pat’s Litchfield Hills Hideaway on 3.0 acres
10.0 (2 Reviews)
3 Bedrooms 8 Guests
Spectacular Cottage at Bantam Lake, Sleeps 12
9.8 (22 Reviews)
7 Bedrooms 12 Guests
Jim & Pat’s Litchfield Hills Lookout on 4.3 acres
9.4 (3 Reviews)
3 Bedrooms 8 Guests
Lakefront Cottage w/Dock, Kayaks
8.6 (12 Reviews)
3 Bedrooms 6 Guests
3 Lake Cottages , Waterfront for 25 Guests
New
13 Bedrooms 16 Guests
Country Winter Retreat
FromCA $246 per night
New
3 Bedrooms 6 Guests
Lakeview Cottage with Dock, Kayaks
9.8 (16 Reviews)
3 Bedrooms 7 Guests
Modern, cozy 3 bedroom lakeside cottage
10.0 (6 Reviews)
3 Bedrooms 8 Guests
Direct Lakefront, Bantam Lake, Private Deer Island
10.0 (3 Reviews)
4 Bedrooms 8 Guests
Sun Filled Direct Lakefront 3 Bedroom House On Bantam Lake
10.0 (1 Review)
3 Bedrooms 6 Guests
The Bethlem Lake House, Lake Side Relaxation!
5.0 (1 Review)
1 Bedroom 2 Guests
Whimsical Cottage in Washington w/ Fire Pit!
4.8 (5 Reviews)
2 Bedrooms 4 Guests
1 of a Kind “IronHorse Farm” All Inclusive retreat
5.0 (9 Reviews)
6 Bedrooms 16 Guests
Charming 3-Bedroom House in Washington
New
3 Bedrooms 5 Guests

About Lakeside Vacation Rentals

With more than 59 Lakeside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) 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 an RBO property in Lakeside.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Lakeside, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO 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 (RBOs), and other popular Airbnb-style properties in Lakeside. Places to stay near Lakeside are 1728.39 ft² on average, with prices averaging CA $954 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Lakeside with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Lakeside?

What are the top vacation rentals in Lakeside?

How many Rentbyowner vacation rentals are available in Lakeside?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 59 in the Lakeside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Lakeside.