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Hotels in Lakeside

October 2026
November 2026

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Check prices for these dates

This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Where to stay in Lakeside?

A hotel room with a large bed, a separate bathroom with a bathtub, and a chair.
A hotel room with a bed, a desk with a computer, a chair, a lamp, and a TV.
A hotel room with a large bed, a desk, a chair, a sofa, and a television.
A hotel room with a TV, a sofa, a coffee table, an air conditioning unit, and a framed picture on the wall.

1. Fairfield by Marriott Inn & Suites New Milford

Fairfield by Marriott Inn & Suites New Milford
New Milford
$134
$146 total
includes taxes & fees
Oct 9 - Oct 10
Fairfield by Marriott Inn & Suites New Milford
A building with a brick exterior, a sliding glass door leading to a room with a bed and a desk, and outdoor seating with chairs.
A view from a covered porch overlooking a grassy field with trees in the background.
A kitchen with a double sink, a coffee maker, and a black refrigerator.
A hotel room with two beds, a bedside table with lamps, a framed picture on the wall, and a wooden floor.

2. Colonial Brick Inn & Suites

Colonial Brick Inn & Suites
Hallstead
$70
$76 total
includes taxes & fees
Oct 23 - Oct 24
Colonial Brick Inn & Suites
A hotel with a sign for rooms and suites, a gym, and a covered outdoor seating area.
A kitchen with wooden cabinets, a stove, microwave, refrigerator, and a dining table with chairs.
An outdoor patio with multiple tables and chairs, a wooden pergola, and a view of the street.
A row of treadmills and elliptical machines in a gym.

3. The Inn at Montrose

The Inn at Montrose
Montrose
$135
$147 total
includes taxes & fees
Oct 1 - Oct 2
The Inn at Montrose
A stone building with red-framed windows and doors, outdoor flower planters, and a hanging flower basket.
A restaurant with wooden walls and a brick fireplace. Tables are set with blue tablecloths and menus.
A wooden deck with railings, a staircase leading to a covered area, and a small building with a window.
A wooden building with a covered porch and a picnic table.

4. Lakewood Lodge

Lakewood Lodge
Lakewood
$121
$132 total
includes taxes & fees
Oct 4 - Oct 5
Lakewood Lodge
A room with a flat-screen TV on a black dresser, white doors, and a carpeted floor.
A building with a porch, a red door, and a flag.
A hotel room with a bed, a nightstand with a lamp, a picture on the wall, and a door.
A compact hotel room with a kitchenette, a television, a small dining table, and a sofa.

5. The Montrose Hotel

The Montrose Hotel
Montrose
$135
$147 total
includes taxes & fees
Oct 12 - Oct 13
The Montrose Hotel
A bedroom with a bed, a large window, a wall-mounted TV, a sink, and a view of a mountainous landscape.
A spacious living area with a green sofa, a white couch, and a wooden bench. There is a chandelier hanging from the ceiling and a large window with curtains.
A modern living room with a sectional sofa, a blue armchair, and two round coffee tables.
A compact kitchen with a black refrigerator, wooden shelves, a wooden countertop, a sink, and a decorative deer head.

6. Green Acres Retreat

Green Acres Retreat
Hancock
$129
$142 total
includes taxes & fees
Oct 5 - Oct 6
Green Acres Retreat
A wooden deck with outdoor seating, a dock, and a view of a lake with a flagpole and a gazebo.
A wooden-floored lobby with a stone fireplace, wooden chairs, a table with a floral centerpiece, and a bar area with a person behind the counter.
A cozy wooden interior with a dining area, a fireplace, and a television.
A restaurant with wooden ceilings, large windows, and tables with chairs.

7. Chestnut Inn at Oquaga Lake

Chestnut Inn at Oquaga Lake
Deposit
$212
$276 total
includes taxes & fees
Oct 1 - Oct 2
Chestnut Inn at Oquaga Lake
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.
A cozy living room with a sofa, a bed, a TV, and a coffee table.
A dining area with a wooden table set for six, surrounded by chairs. A wooden cabinet with glass doors is to the left, and a television is mounted on the wall to the right.
A two-story house with a front porch and a staircase leading to the entrance.

8. Hale Eddy

Hale Eddy
Hancock
$155
$331 total
includes taxes & fees
Oct 1 - Oct 2
Hale Eddy
View all properties

Go beyond your typical stay in Lakeside

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Pet friendly
Pet friendly
Pool image
Pool
Pool
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Hot tub
Hot tub
Family friendly image
Family friendly
Family friendly
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Apart hotel
Apart hotel
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Cottage
Cottage

Check out reviews of Lakeside hotels guests love

A bedroom with a bed, a large window, a wall-mounted TV, a sink, and a view of a mountainous landscape.
A spacious living area with a green sofa, a white couch, and a wooden bench. There is a chandelier hanging from the ceiling and a large window with curtains.
A modern living room with a sectional sofa, a blue armchair, and two round coffee tables.
A compact kitchen with a black refrigerator, wooden shelves, a wooden countertop, a sink, and a decorative deer head.

Green Acres Retreat

Green Acres Retreat
Hancock

10/10 Exceptional

United States
Kari
Green Acres Retreat
A wooden deck with outdoor seating, a dock, and a view of a lake with a flagpole and a gazebo.
A wooden-floored lobby with a stone fireplace, wooden chairs, a table with a floral centerpiece, and a bar area with a person behind the counter.
A cozy wooden interior with a dining area, a fireplace, and a television.
A restaurant with wooden ceilings, large windows, and tables with chairs.

Chestnut Inn at Oquaga Lake

Chestnut Inn at Oquaga Lake
Deposit

10/10 Exceptional

United States
Robert
Chestnut Inn at Oquaga Lake
A room with a flat-screen TV on a black dresser, white doors, and a carpeted floor.
A building with a porch, a red door, and a flag.
A hotel room with a bed, a nightstand with a lamp, a picture on the wall, and a door.
A compact hotel room with a kitchenette, a television, a small dining table, and a sofa.

The Montrose Hotel

The Montrose Hotel
Montrose

10/10 Exceptional

United States
Anonymous traveler
The Montrose Hotel
A hotel room with a large bed, a separate bathroom with a bathtub, and a chair.
A hotel room with a bed, a desk with a computer, a chair, a lamp, and a TV.
A hotel room with a large bed, a desk, a chair, a sofa, and a television.
A hotel room with a TV, a sofa, a coffee table, an air conditioning unit, and a framed picture on the wall.

Fairfield by Marriott Inn & Suites New Milford

Fairfield by Marriott Inn & Suites New Milford
New Milford

10/10 Exceptional

United States
Angel
Fairfield by Marriott Inn & Suites New Milford
A building with a brick exterior, a sliding glass door leading to a room with a bed and a desk, and outdoor seating with chairs.
A view from a covered porch overlooking a grassy field with trees in the background.
A kitchen with a double sink, a coffee maker, and a black refrigerator.
A hotel room with two beds, a bedside table with lamps, a framed picture on the wall, and a wooden floor.

Colonial Brick Inn & Suites

Colonial Brick Inn & Suites
Hallstead

10/10 Exceptional

United States
Griseldi
Colonial Brick Inn & Suites
A stone building with red-framed windows and doors, outdoor flower planters, and a hanging flower basket.
A restaurant with wooden walls and a brick fireplace. Tables are set with blue tablecloths and menus.
A wooden deck with railings, a staircase leading to a covered area, and a small building with a window.
A wooden building with a covered porch and a picnic table.

Lakewood Lodge

Lakewood Lodge
Lakewood

10/10 Exceptional

United States
Bruce
Lakewood Lodge
A hotel with a sign for rooms and suites, a gym, and a covered outdoor seating area.
A kitchen with wooden cabinets, a stove, microwave, refrigerator, and a dining table with chairs.
An outdoor patio with multiple tables and chairs, a wooden pergola, and a view of the street.
A row of treadmills and elliptical machines in a gym.

The Inn at Montrose

The Inn at Montrose
Montrose

10/10 Exceptional

United States
Sean
The Inn at Montrose

Frequently Asked Questions

What hotels do travelers like in Lakeside?

Guests like Colonial Brick Inn & Suites and Fairfield by Marriott Inn & Suites New Milford.

Can I book refundable accommodations in Lakeside?

If you're looking for the flexibility to change your travel plans to Lakeside, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

What will the weather in Lakeside be like during my trip?

The warmest months in Lakeside are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are June and September.

Why should I book my Lakeside accommodation with Hotels.com?

There are lots of reasons to book your Lakeside trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.