A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Winchester 2 Stars Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester 2 Star Hotels

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Winchester 2-star hotels

A hotel with a swimming pool, parking lot, and a view of a lake.
A conference room with a large table and chairs, a television, and a view of a park with trees and a body of water.
A modern living room with a unique curved sofa, a large mirror, and a kitchen area with a bar.
A modern lobby with a reception desk, seating area, and a staircase.

1. Lakeside Inn

Lakeside Inn
Wakefield
United States
Marc
NT$2,829
NT$3,160 total
includes taxes & fees
Sep 1 - Sep 2
Lakeside Inn
A living room with a fireplace, a television mounted on the wall, and a large potted plant.
A hotel room with a bed, two bedside tables with lamps, a TV, a desk, and a chair.
An outdoor patio with a round table and chairs, a large umbrella, and a pool in the background.
A hotel room with a kitchenette, a dining area, and a TV mounted on the wall.

2. Ramada by Wyndham Boston

Ramada by Wyndham Boston
Dorchester
United States
Yvette
NT$3,845
NT$4,477 total
includes taxes & fees
Sep 7 - Sep 8
Ramada by Wyndham Boston

3. Extended Stay America Suites Boston Burlington

Extended Stay America Suites Boston Burlington
Burlington
United States
David
NT$3,215
NT$3,592 total
includes taxes & fees
Sep 1 - Sep 2
Extended Stay America Suites Boston Burlington
A modern living room with a fireplace, a dining area, and a bar with stools.
A gym with treadmills, elliptical machines, and free weights.
A vending machine stocked with snacks and drinks, surrounded by shelves with packaged goods.
A hotel room with a bed, a TV on a wooden stand, a desk with drawers, a microwave, and a mirror on the wall.

4. Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea
Chelsea
United States
Tammi
NT$5,297
NT$5,917 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn Boston Logan Airport Chelsea
A spacious lobby with a high ceiling, wooden paneling, a large sofa, and a coffee table.
A hotel room with a four-poster bed, a desk with a laptop, a sofa, and a view of the city through the window.
An outdoor patio with stone walls, a pool table, and seating areas.
A bar area with a long counter, multiple stools, and a neon sign.

5. Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
Revere
United States
Jane
NT$5,197
NT$5,994 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Logan International Airport

6. Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Woburn
United States
Darventz
NT$3,352
NT$3,744 total
includes taxes & fees
Sep 7 - Sep 8
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
A hotel room with a bed, bedside tables, a desk, a TV, and a wardrobe.
A motel with a parking lot, several trees, and a building with a sloped roof.
A reception area with a marble counter, a 'Welcome' sign, a 'Be Our Guest' sign, a Wi-Fi sign, and a view of the outdoors.
A hotel sign with the name 'Northshore Hotel' and address '219 Newbury Street'.

7. The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers
Danvers
United States
Sean
NT$3,225
NT$3,602 total
includes taxes & fees
Sep 1 - Sep 2
The Northshore Hotel - Boston/Danvers
A modern kitchen with a bar area, wooden dining table, and bar stools.
A brick building with a sign reading "enVision Hotel" on the corner.
A spacious lounge area with seating, a fireplace, and a bookshelf.
A hotel room with a large bed, a headboard with a map, and a window with curtains.

8. enVision Hotel Boston Everett

enVision Hotel Boston Everett
Everett
Canada
Guillaume
NT$4,044
NT$4,518 total
includes taxes & fees
Aug 31 - Sep 1
enVision Hotel Boston Everett

9. Red Roof Inn PLUS+ Boston - Logan

Red Roof Inn PLUS+ Boston - Logan
Saugus
Canada
Diana
NT$3,171
NT$3,542 total
includes taxes & fees
Sep 9 - Sep 10
Red Roof Inn PLUS+ Boston - Logan
A modern hotel with a prominent 'Avid' sign, large windows, and a well-lit entrance.
A clean, modern food and beverage area with refrigerated drinks, snacks, and a variety of packaged goods.
A modern interior with a market area, seating, and a counter.
A city skyline with modern buildings, a river with sailboats, and a park with trees.

10. avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG
Revere
United States
Nancee
NT$5,122
NT$5,721 total
includes taxes & fees
Sep 7 - Sep 8
avid hotel Boston Logan Airport - Revere by IHG
A hotel room with two beds, a wooden headboard, bedside lamps, a nightstand, and a phone.
A Holiday Inn Express hotel with a covered entrance and multiple floors.
An indoor swimming pool with clear water, a diving board, and a poolside area with chairs and a wooden cabinet.
A modern indoor space with seating arrangements, tables, and a view through large windows.

11. Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG
Chelmsford
United States
Maria Del Carmen
NT$3,472
NT$3,878 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn Express Chelmsford by IHG
A modern living room with a fireplace, seating area, and large windows.
A hotel room with a bed, a desk with a TV, a large window with curtains, and a city view.
A modern hotel lobby with round tables, comfortable seating, large windows, and a view of the city.
A modern interior with a brick wall, glass railings, and a seating area with cushions.

12. Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
Watertown
United States
Gilsoon
NT$4,945
NT$5,524 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn & Suites Watertown Boston
A hotel room with a large bed, a desk, and a chair. There is a window with curtains, a lamp, and a framed picture on the wall.
A multi-story brick building with a fire escape, a sign for 'Hotel IVY', and a tree in front.
A marble wall with a decorative relief and a brass handrail.
A modern hotel lobby with a black brick wall, two pendant lights, a wooden table, and a bookshelf filled with decorative items.

13. Hotel Ivy Boston Common

Hotel Ivy Boston Common
Bay Village
United Kingdom
Rebekah
NT$5,663
NT$6,595 total
includes taxes & fees
Sep 7 - Sep 8
Hotel Ivy Boston Common
A modern reception area with a white desk, two computer monitors, a blue sofa, and a green chair.
An outdoor patio with wicker furniture and a fire pit.
A hotel lobby with a blue sofa, green armchairs, and a patterned rug.

14. Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel
Danvers
United States
Jie
NT$4,269
NT$4,768 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus North Shore Hotel
A building entrance with a doormat, large windows, and potted plants.
A balcony with wicker chairs and a view of the cityscape.
A round table with a teapot and biscuits by a window with a view of a building with a tower.
A modern room with large windows, a round table, and four chairs.

15. Lark Hotels 907 Main

Lark Hotels 907 Main
Central Square
United States
SUSAN
NT$4,584
NT$5,316 total
includes taxes & fees
Sep 7 - Sep 8
Lark Hotels 907 Main
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern building with a covered entrance, multiple windows, and a parking lot.
A modern kitchen with grey cabinetry, a black countertop, and a vase with yellow flowers.
A modern kitchen with grey cabinetry, a black countertop, and a yellow chair.

16. The Inn on Arsenal

The Inn on Arsenal
Watertown
United States
Brian
NT$4,221
NT$4,715 total
includes taxes & fees
Aug 31 - Sep 1
The Inn on Arsenal
A modern hotel with a covered entrance, multiple floors, and a landscaped area in front.
A modern kitchen with a bar area, bar stools, pendant lighting, and a large TV.
A modern building with large windows, outdoor seating, and a well-maintained garden.
A modern kitchen with a central island, bar seating, and a variety of food items displayed.

17. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
United States
Charles Richard Losh
NT$3,785
NT$4,228 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn Boston Woburn
A marina with boats docked, a wooden walkway, and buildings in the background.
A hotel room with a large bed, a desk with a chair, a television, and a window with curtains.
A wooden pier with a gazebo, a view of the sunset, and a river.
A riverside hotel with a dock and a gazebo.

18. Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston
Quincy
Canada
Leanne
NT$4,810
NT$5,372 total
includes taxes & fees
Sep 13 - Sep 14
Best Western Adams Inn Quincy-Boston
A modern restaurant with a central counter, multiple dining tables, and chairs.
A modern hotel entrance with a covered walkway, a glass facade, and a landscaped area with shrubs and trees.
A modern hotel lobby with a seating area featuring blue upholstered sofas, a coffee table with a vase of flowers, and a large flat-screen TV mounted on a dark wall.
A hotel room with a desk, two beds, a TV, a lamp, and a painting on the wall.

19. Best Western Plus New Englander

Best Western Plus New Englander
Woburn
United States
Victor
NT$3,589
NT$4,009 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Plus New Englander
A modern dining area with high ceilings, large windows, and a prominent poster on the wall.
A modern lobby with large windows, multiple seating areas, and a visible staircase.
A modern lounge area with a large TV screen, comfortable seating, and a fireplace.

20. HI Boston - Hostel

HI Boston - Hostel
Bay Village
United States
Miriam
NT$5,976
NT$6,959 total
includes taxes & fees
Sep 7 - Sep 8
HI Boston - Hostel
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Winchester.
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

220 Huntington Avenue Boston MA
NT$5,976
NT$6,959 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (968 reviews)
The Midtown Hotel MOD Collection by Sonesta
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

5 Blossom Street Boston MA
NT$6,802
NT$7,920 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (2,200 reviews)
Wyndham Boston Beacon Hill
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

4 Highwood Drive Tewksbury MA
NT$3,063
NT$3,422 total
Sep 20 - Sep 21
includes taxes & fees
9/10 Wonderful! (1,376 reviews)
Hilton Garden Inn Tewksbury Andover
Still don't see what you're looking for?
See all properties in Winchester.
You can also use these popular filters to refine your search.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

See all hotels in Winchester
A historic building with a clock tower, red brick walls, and a green roof.

Top Winchester Hotel Reviews

Explore a world of travel with Expedia