The Best Cheap Hotels in Winchester, MA from $88 - Winchester Cheap Hotels

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Our top choices for Winchester cheap hotels

A spacious lobby with a reception desk, seating area, and a large TV screen.

1. Crowne Plaza Boston - Woburn by IHG

Woburn

Khawla

$110 nightly

Nov 22 - Nov 23

Total with taxes and fees

A hotel with a swimming pool, parking lot, and a view of a lake.

2. Lakeside Inn

Wakefield

Richard

$79 nightly

Nov 18 - Nov 19

Total with taxes and fees

A Staybridge Suites hotel with a stone facade, multiple windows, and a covered entrance area.

3. Staybridge Suites Boston - Burlington by IHG

Burlington

Kristie

$131 nightly

Nov 28 - Nov 29

Total with taxes and fees

A multi-story hotel with a parking lot in front, featuring a covered entrance and multiple windows.

4. La Quinta Inn & Suites by Wyndham Boston Somerville

Assembly Square

James Allen

$90 nightly

Dec 6 - Dec 7

Total with taxes and fees

A hotel room with a large bed, a desk, a chair, a television, and a wardrobe.

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

Woburn

Stefany

$97 nightly

Nov 19 - Nov 20

Total with taxes and fees

A modern lobby with a leather sofa, two round wooden tables, a flat-screen TV mounted on a textured wall, and a glass partition with a view of the outdoors.

6. Four Points by Sheraton Boston Newton

Newton Corner

Patricia

$93 nightly

Dec 6 - Dec 7

Total with taxes and fees

A modern bar area with a long counter, bar stools, and a television screen.

7. Hampton Inn Boston - Logan Airport

Revere

Paul

$97 nightly

Nov 25 - Nov 26

Total with taxes and fees

A spacious lobby with a high ceiling, wooden paneling, a large sofa, and a coffee table.

8. Comfort Inn & Suites Logan International Airport

Revere

Anthony

$122 nightly

Dec 6 - Dec 7

Total with taxes and fees

A modern living room with a fireplace, a dining area, and a bar with stools.

9. Hampton Inn Boston Logan Airport Chelsea

Chelsea

Edwin J Ruiz

$110 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern hotel with a prominent 'Avid' sign, large windows, and a well-lit entrance.

10. avid hotel Boston Logan Airport - Revere by IHG

Revere

Carleen

$103 nightly

Dec 14 - Dec 15

Total with taxes and fees

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Find out more about Winchester

How can I get cheap hotels in Winchester?

Best tips to find a cheap hotel in Winchester

If you're looking to travel to Winchester on a budget, you'll be happy to know that you can find hotels for as low as $88. Of course, that price is affected by amenities, star rating, and even the time of year you visit. At most, hotel prices can be as high as $162. Staying a short amount of time in Winchester is an effective way to reduce hotel costs.
When you cut your vacation down to just a few days, you don't have to worry as much about hotel prices since you don't have that many nights to stay. For budget hotels in Winchester, 3 to 4 days should be all the nights you need. That's generally enough to enjoy the city's top attractions, though there's certainly enough to do to warrant a week-long trip.
When booking cheap hotel rooms in Winchester, it's typically best to book about 3 weeks in advance. Book further in advance than that and you could be paying too much for your room, as hotels will often overestimate future demand. However, if you wait too long, you might find that the hotel has been completely booked.
When you utilize search filters on Expedia, you'll be able to narrow down your results in a flash. These search filters cover a wide variety of factors you may be interested in when it comes to finding a cheap hotel in Winchester, including amenities such as Free Breakfast, 2-star rating, or proximity to local attractions. You can even set filters for price limits to ensure that all the displayed results are within your budget.

Top Winchester Hotel Reviews

Harborside Inn Of Boston

8/10 Good

"Rooms are clean, small and simple. Felt like a dorm room like vibe to us. Location is great and an overall nice property with a nice restaurant on the premises."

Omni Parker House

10/10 Excellent

"I stayed at the historic, stunning Omni Parker House with my husband and 13 year old son, and we all agree - we couldn’t recommend it more highly. Our stay was fantastic! Every staff member we encountered was incredibly kind and helpful. The hotel is perfectly situated - it’s right in the middle of everything. And - don’t miss the restaurant!"

Hilton Boston Park Plaza

8/10 Good

"This hotel is an older hotel, and some of the reviews I saw before staying there gave me pause, saying that other than the lobby area it was frowsy and dated. I thought the hotel was very nice. It clearly wasn’t renovated yesterday but our room, although VERY small, was quite nice. The location was outstanding (given what we were doing in the area) and the price was reasonable. I would certainly stay there again. We didn’t use any of the amenities so I can’t speak to those. We self parked in a nearby garage by reserving ahead of time and got a good price for that. We didn’t eat in the restaurant. What I didn’t like - that they charge a resort fee, and we were there for just one night and didn’t get to use the $15 credit for food/drink in the restaurant. The room and bathroom were the smallest I’ve ever stayed in. We had an opty to upgrade at a discount but for one night we didn’t bother. The check in person even said “they put you in a wicked small room” and he wasn’t kidding! The bathroom was so small I had to wrap the shower curtain up over the rod because you couldn’t even sit on the toilet without it being in your face. If you are staying multiple days - take the upgrade! Bed was fine, pillows were hard."

Frequently asked questions

What is Winchester like for travelers on a budget?

Check out cheap places to stay in Winchester on Expedia.com and plan a trip that matches your budget. You can scroll through a wide offering of accommodation choices with Member Prices to find great deals. With our site's handy page filters, you can search by price per night, or by top amenities like free breakfast and a swimming pool. If you're interested in affordable options near specific attractions, such as Winter Pond or Middlesex Fells Reservation, try filtering by location to refine your search. As you browse, click the heart button to keep track of your favorites so that you can return to them easily and make your final decision. Need a flight or a car for your trip? Take a look at the Bundle and Save vacation packages and discover more amazing deals when you reserve your transportation at the same time.

When is the best time for a budget trip to Winchester?

Weather will likely play an important role when you plan your trip to Winchester, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.

What is there to see and do in Winchester?

You don't need to spend big to find places to visit in Winchester. You can budget for the top local attractions that interest you most, such as Fenway Park and Encore Boston Harbor, and then look for sights and activities that cost little or nothing at all. Check out the area's cultural spots like Somerville Theatre and Harvard Museum of Natural History, or get outdoors at Winter Pond.

How can I get to Winchester and get around on a budget?

Scoping out the transportation options in Winchester can help keep you on budget. The closest airport is 7.7 mi (12.3 km) away from the center in Bedford, MA (BED-Laurence G. Hanscom Field). However, if that doesn't suit your budget, you can book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), located 8.4 mi (13.5 km) away. To see more of the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station.

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Our top choices for Winchester cheap hotels

1. Crowne Plaza Boston - Woburn by IHG

2. Lakeside Inn

3. Staybridge Suites Boston - Burlington by IHG

4. La Quinta Inn & Suites by Wyndham Boston Somerville

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

6. Four Points by Sheraton Boston Newton

7. Hampton Inn Boston - Logan Airport

8. Comfort Inn & Suites Logan International Airport

9. Hampton Inn Boston Logan Airport Chelsea

10. avid hotel Boston Logan Airport - Revere by IHG

Find out more about Winchester

How can I get cheap hotels in Winchester?

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Omni Parker House

Wyndham Boston Beacon Hill

Ramada by Wyndham Boston

Hilton Boston Park Plaza

Frequently asked questions

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