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

Compare and book 2 Star hotels in Winchester, Boston

  • 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
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Winchester 2-star hotels

A hotel with a swimming pool, parking lot, and a view of a lake.
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 large mirror on the wall.
A modern lobby with a reception desk, seating area, and a staircase.

1. Lakeside Inn

Lakeside Inn
Wakefield
United States
Robert
2.812.756 ₫
3.141.848 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Lakeside Inn
Indoor pool
A modern living room with a fireplace, blue sofas, a brown leather chair, and a colorful rug.
A hotel lobby with a blue sofa, green armchairs, and a patterned rug.
An outdoor patio with wicker furniture and a fire pit.

2. Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel
Danvers
United States
Nancy
3.281.161 ₫
3.665.057 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Best Western Plus North Shore Hotel
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
A laundry room with three washing machines, a sign for soap, bleach, and softeners, and a sign warning not to leave unattended items.
A reception desk with a large number '6' on the wall, two digital screens displaying a booking message, and a tiled floor.
A hallway with vending machines, including Pepsi, and a brick wall.

3. Motel 6 Danvers, MA - Boston North

Motel 6 Danvers, MA - Boston North
Danvers
United States
Yahaira
4.013.156 ₫
4.482.695 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Motel 6 Danvers, MA - Boston North
A marina with boats docked, a wooden walkway, and buildings in the background.
A long, dark wood-paneled counter with a variety of food items and appliances, large windows with arched tops, and a high ceiling with recessed lighting.
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.

4. Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston
Quincy
United States
Clare
3.006.436 ₫
3.358.189 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Best Western Adams Inn Quincy-Boston
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern kitchen with grey cabinetry, a black countertop, and a vase with yellow flowers.
A bathroom with a white sink, mirror, and shower curtain.
A modern building with a covered entrance, multiple windows, and a parking lot.

5. The Inn on Arsenal

The Inn on Arsenal
Watertown
United States
Donna
3.090.017 ₫
3.451.549 ₫ total
includes taxes & fees
12 Nov - 13 Nov
The Inn on Arsenal
A hotel room with two red armchairs, a small round table, a floor lamp, and two potted plants.
A modern hotel room with a wooden floor, a large bed with patterned bedding, a desk with a chair, a flat-screen TV, and a window with curtains.
A motel sign with a large number 6 and the text "WI FI HERE" indicating the availability of Wi-Fi.
A reception area with a potted plant, a coffee station with red dispensers, and a sign that reads "RISE & SHINE".

6. Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West
Framingham
United States
Aiyanna
2.485.469 ₫
2.828.055 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Motel 6 Framingham, MA - Boston West
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 with a modern facade, a parking lot, and two parked cars.

7. enVision Hotel Boston Everett

enVision Hotel Boston Everett
Everett
United States
Angela
2.762.886 ₫
3.086.143 ₫ total
includes taxes & fees
10 Nov - 11 Nov
enVision Hotel Boston Everett
A lobby with seating, a reception desk, and a refrigerator stocked with beverages.
A coffee station with two coffee machines, a coffee press, and various coffee-related items on a counter.
A Holiday Inn Express & Suites building with a modern design, featuring a large sign, a covered entrance, and a landscaped front yard.
A coffee station with two coffee machines, a sign reading "UMUST. HAVE. COFFEE.", and various coffee-related items on shelves.

8. Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG
Chelmsford
United States
John
2.726.533 ₫
3.045.538 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Chelmsford by IHG
A modern kitchen with stainless steel appliances, wooden cabinets, and a white countertop.
A kitchenette with a microwave, coffee machine, and trash bin.
A coffee station with two espresso machines, a coffee display, and a sign that reads 'MUST HAVE COFFEE.'
A Keurig coffee machine with a coffee pod holder and a tray with coffee cups.

9. Holiday Inn Express Boston North-Woburn by IHG

Holiday Inn Express Boston North-Woburn by IHG
Woburn
United States
GOUTHAM
2.951.802 ₫
3.297.163 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Boston North-Woburn by IHG
A modern living room with a sofa, a dining table, and chairs. There is a kitchen area with cabinets and a microwave.
A multi-story hotel with a brick facade and a sign for 'Sonesta Simply Suites'.
A hotel room with a bed, a sofa, a small table, a TV, and a window with curtains.
A covered outdoor seating area with a grill, chairs, and tables.

10. Sonesta Simply Suites Boston Burlington

Sonesta Simply Suites Boston Burlington
Burlington
United States
Cara A
2.459.835 ₫
2.747.636 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Sonesta Simply Suites Boston Burlington
A modern living room with a fireplace, seating area, and large windows.
A multi-story hotel with a modern design, featuring a prominent 'Hampton Inn' sign, a 'Buffalo Wild Wings' restaurant, and a 'Premier Dental' clinic.
A modern hotel lobby with round tables, comfortable seating, large windows, and a view of the city.
A hotel room with a bed, a desk with a TV, a large window with curtains, and a city view.

11. Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston
Watertown
United States
Emma
4.163.405 ₫
4.650.524 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Watertown Boston
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 restaurant with tables and chairs, a television, and a fireplace.
A hotel sign with the name 'Northshore Hotel' and address '219 Newbury Street'.

12. The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers
Danvers
United States
Pamela
2.565.684 ₫
2.865.869 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Northshore Hotel - Boston/Danvers
A living room with a fireplace, a television mounted on the wall, and a large potted plant.
A reception area with a wooden reception desk, a potted plant, a clock, and a bench.
A hotel room with a bed, two bedside tables with lamps, a TV, a desk, and a chair.
A hotel room with a kitchenette, a dining area, and a TV mounted on the wall.

13. Ramada by Wyndham Boston

Ramada by Wyndham Boston
Dorchester
United States
Nazli
2.361.442 ₫
2.749.898 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Ramada by Wyndham Boston
A lobby with leather chairs, a table with a vase of flowers, a framed picture, and a staircase with yellow curtains.
A hotel room with a red sofa, a wooden cabinet, a television, and a refrigerator.
A building with a brick facade, white columns, and a covered entrance.
A hotel room with two beds, a desk with a computer, a chair, and a TV.

14. Charles River Inn

Charles River Inn
Brighton
United States
Nancy
3.751.896 ₫
4.368.926 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Charles River Inn
A lobby with two leather armchairs, a small table, a reception desk, and a wall-mounted sign reading 'Red Roof Plus'.
Room
A hotel room with a large bed, a desk, a chair, a television, and a wardrobe.
A compact kitchen with a refrigerator, a coffee machine, and a washing machine.

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

Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Woburn
United States
REBECCA
2.299.161 ₫
2.568.163 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
A spacious lobby with a high ceiling, wooden paneling, a large sofa, and a coffee table.
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.
An indoor swimming pool with a tiled floor, a wooden ceiling, and a seating area with orange cushions.

16. Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
Revere
United States
James
3.850.599 ₫
4.456.615 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Comfort Inn & Suites Logan International Airport
Shared kitchen facilities
A multi-story building with large windows and a brick facade.
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.

17. HI Boston - Hostel

HI Boston - Hostel
Bay Village
United States
Mairead
5.831.100 ₫
6.790.769 ₫ total
includes taxes & fees
9 Nov - 10 Nov
HI Boston - Hostel
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 hotel room with a bed, a TV on a wooden stand, a desk with drawers, a microwave, and a mirror on the wall.
A vending machine stocked with snacks and drinks, surrounded by shelves with packaged goods.

18. Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea
Chelsea
United States
Nicole
3.392.404 ₫
3.789.315 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Hampton Inn Boston Logan Airport Chelsea
A hallway with a door marked 'EXIT' and a sign indicating 'STAIR 2 FLOOR 1 No Roof Access'.
A hotel room with a flat-screen TV mounted on the wall, a desk with a chair, a sofa, a small table, and a kitchenette area.
A hotel room with a bed, a desk, a television, and a window with curtains.
A Red Roof Plus hotel with a parking lot and a covered entrance.

19. Red Roof Inn PLUS+ Boston - Logan

Red Roof Inn PLUS+ Boston - Logan
Saugus
United States
Kristy
2.268.687 ₫
2.534.067 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Red Roof Inn PLUS+ Boston - Logan
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 modern hotel lobby with a black brick wall, two pendant lights, a wooden table, and a bookshelf filled with decorative items.
A marble wall with a decorative relief and a brass handrail.
A multi-story brick building with a fire escape, a sign for 'Hotel IVY', and a tree in front.

20. Hotel Ivy Boston Common

Hotel Ivy Boston Common
Bay Village
United States
Tiffany
3.757.561 ₫
4.375.680 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Hotel Ivy Boston Common
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
4.660.740 ₫
5.427.431 ₫ total
9 Nov - 10 Nov
includes taxes & fees
8/10 Very good! (1,255 reviews)
The Midtown Hotel MOD Collection by Sonesta
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

4 Highwood Drive Tewksbury MA
2.207.119 ₫
2.465.272 ₫ total
8 Nov - 9 Nov
includes taxes & fees
Hilton Garden Inn Tewksbury Andover
Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

50 Forbes Road Braintree MA
2.927.204 ₫
3.269.687 ₫ total
15 Nov - 16 Nov
includes taxes & fees
Hyatt Place Boston/Braintree
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
An aerial view of a town with a lake, church steeples, and a bridge.

Top Winchester Hotel Reviews

Explore a world of travel with Expedia