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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Condo Rentals in Winchester

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marina

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

10.0 out of 10, Exceptional, (66)
"I was beyond impressed with my stay here in Marblehead! As a solo traveler, I felt safe in this Vrbo property. Everything was beyond clean, access was easy, and having a dedicated parking spot was amazing. It was the perfect place to stay!"
The price is SAR 587
SAR 1,263 total
includes taxes & fees
3 Nov - 4 Nov
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Suite at House of L: near Boston, Hospitals, Encore Casino, Walk to Bus, Fast WiFi, Driveway
Beach

Suite at House of L: near Boston, Hospitals, Encore Casino, Walk to Bus, Fast WiFi, Driveway

9.0 out of 10, Wonderful, (30)
"Good location with a quick drive to downtown areas, property felt safe and secure, comfortable bedding, good for a weekend trip to Boston! Well stocked with supplies, I appreciated having the off street parking spot, I enjoyed the small space with seating area outside. The tenants upstairs were not loud overnight which was much appreciated. "
The price is SAR 454
SAR 1,398 total
includes taxes & fees
27 Oct - 28 Oct
Suite at House of L: near Boston, Hospitals, Encore Casino, Walk to Bus, Fast WiFi, Driveway
Modern & Stylish 1-Bedroom Condo near Downtown
In-room safe, desk, iron/ironing board, free WiFi

Modern & Stylish 1-Bedroom Condo near Downtown

10.0 out of 10, Exceptional, (4)
"Very nice and quiet neighborhood. Would love to rent again if the opportunity presents itself. "
The price is SAR 503
SAR 1,402 total
includes taxes & fees
13 Oct - 14 Oct
Modern & Stylish 1-Bedroom Condo near Downtown
Village Retreat: Walk to Charming Historic Town, Off Street Parking, Private Deck, Grill
On the beach, fishing

Village Retreat: Walk to Charming Historic Town, Off Street Parking, Private Deck, Grill

2.0 star property
The price is SAR 1,185
SAR 2,417 total
includes taxes & fees
16 Oct - 17 Oct
Village Retreat: Walk to Charming Historic Town, Off Street Parking, Private Deck, Grill
Lg suite for up to 8 ppl/2 floor
Dining

Lg suite for up to 8 ppl/2 floor

10.0 out of 10, Exceptional, (12)
"The apartment was perfect, just as advertised. Very clean and comfortable. Would not hesitate to stay there again."
The price is SAR 581
SAR 1,850 total
includes taxes & fees
14 Oct - 15 Oct
Lg suite for up to 8 ppl/2 floor
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Outdoor dining

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

10.0 out of 10, Exceptional, (2)
"Very nice and private. Reasonably close to commuter lines into Boston."
The price is SAR 488
SAR 800 total
includes taxes & fees
13 Oct - 14 Oct
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Coastal Charm: Lobster Châto
TV, fireplace

Coastal Charm: Lobster Châto

2.0 star property
8.0 out of 10, Very Good, (3)
"Beautiful house & views,"
The price is SAR 1,922
SAR 3,867 total
includes taxes & fees
13 Oct - 14 Oct
Coastal Charm: Lobster Châto
Stylish home next to train to Boston, near Salem
Smart TV

Stylish home next to train to Boston, near Salem

2.0 star property
10.0 out of 10, Exceptional, (3)
"we were in Massachusetts for our youngest granddaughters college graduation. This place was great. Good location and great hosts! Beautiful neighborhood Easy to walk to breakfast, lunch or dinner. "
The price is SAR 694
SAR 1,713 total
includes taxes & fees
4 Nov - 5 Nov
Stylish home next to train to Boston, near Salem
Great South End / Back Bay location, 1 bed condo near T station
Dining

Great South End / Back Bay location, 1 bed condo near T station

10.0 out of 10, Exceptional, (96)
"The location was outstanding offering easy access to all attractions and public transportation, all while being situated on a quiet street. The host was the best I've ever encountered-extremely responsive and attentive to all our needs. I was concerned about parking since we drove in, but the garage was only 2 blocks away and secure. Dropping off luggage first at the house was no problem. Would stay here again and recommend."
The price is SAR 1,313
SAR 1,970 total
includes taxes & fees
30 Oct - 31 Oct
Great South End / Back Bay location, 1 bed condo near T station
Modern Three Bedroom Condo - Near Boston
Fridge, microwave, oven, stovetop

Modern Three Bedroom Condo - Near Boston

8.8 out of 10, Excellent, (8)
"Two friends and myself went to Boston for a concert and stayed in this house. The description was right on and the house fit our needs. I would rent this property again if i go back to Boston. "
The price is SAR 827
SAR 1,880 total
includes taxes & fees
8 Oct - 9 Oct
Modern Three Bedroom Condo - Near Boston
Your cozy home away from home, close to subway and downtown Boston
Fridge, microwave, oven, stovetop

Your cozy home away from home, close to subway and downtown Boston

9.0 out of 10, Wonderful, (8)
"Great place ideally located."
The price is SAR 656
SAR 1,604 total
includes taxes & fees
30 Oct - 31 Oct
Your cozy home away from home, close to subway and downtown Boston
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Fridge, microwave, oven, stovetop

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

10.0 out of 10, Exceptional, (27)
"Excellent place for our stay during my daughter's graduation at Tufts. "
The price is SAR 807
SAR 1,794 total
includes taxes & fees
26 Oct - 27 Oct
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Fridge, microwave, oven, stovetop

🎖The Ashmont Suite - Close to Subway + Downtown🎖

10.0 out of 10, Exceptional, (53)
"The historic Victorian home is amazing! So much space and has everything you would need for a great stay. "
The price is SAR 934
SAR 1,819 total
includes taxes & fees
26 Oct - 27 Oct
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Bright & Spacious Loft Steps to the Freedom Trail
Smart TV, books

Bright & Spacious Loft Steps to the Freedom Trail

10.0 out of 10, Exceptional, (48)
"Great apartment and well stocked kitchen close to Boston's freedom trail and best sites."
The price is SAR 1,566
SAR 2,598 total
includes taxes & fees
24 Oct - 25 Oct
Bright & Spacious Loft Steps to the Freedom Trail
Lovely Two Bedroom Condo in South Boston
Exterior detail

Lovely Two Bedroom Condo in South Boston

7.8 out of 10, Good, (6)
"Very clean "
The price is SAR 941
SAR 2,131 total
includes taxes & fees
20 Oct - 21 Oct
Lovely Two Bedroom Condo in South Boston
Stunning Waterfront Condo with Boston Skyline Views
Exterior detail

Stunning Waterfront Condo with Boston Skyline Views

10.0 out of 10, Exceptional, (5)
"The condo is exactly as listed: spacious, comfortable, beautiful. The outdoor space is fantastic. Love the neighborhood: can walk to the waterfront park which is lovely; view of Boston over the harbor, and access Boston proper very easily. The hosts and manager are amazing at communicating and responded promptly to all questions. This is a very perfect rental. "
The price is SAR 1,301
SAR 3,432 total
includes taxes & fees
5 Nov - 6 Nov
Stunning Waterfront Condo with Boston Skyline Views
Back-Bay Upscale Central Condo Bos Common Downtown
Terrace/patio

Back-Bay Upscale Central Condo Bos Common Downtown

10.0 out of 10, Exceptional, (7)
"Great location for this apartment. Check in was a breeze. Would definitely come back and stay here!"
The price is SAR 1,770
SAR 4,276 total
includes taxes & fees
29 Oct - 30 Oct
Back-Bay Upscale Central Condo Bos Common Downtown
Large victorian home 15 mins from downtown lots of local restaurants and bars
Microwave, oven, stovetop, dishwasher

Large victorian home 15 mins from downtown lots of local restaurants and bars

8.6 out of 10, Excellent, (4)
"Host was quick to respond and helpful. It had very spacious living area. There is a king bed, all the "queen" beds were actually doubles. There were bath towels but no washcloths. There was a Keurig, not coffee maker as advertised. It was sufficient for our two day stay. We had a great visit to Boston. The house location was easy driving to the harbor walk and seaport district. We were able to Uber relatively cheap to Fenway and downtown Boston. It was overall a good experience with this host. ...
The price is SAR 2,194
SAR 4,605 total
includes taxes & fees
8 Oct - 9 Oct
Large victorian home 15 mins from downtown lots of local restaurants and bars
Designer Oceanfront Retreat Featured in Architectural Digest ☀ Steps from Beach
Outdoor pool

Designer Oceanfront Retreat Featured in Architectural Digest ☀ Steps from Beach

10.0 out of 10, Exceptional, (3)
"Very nice house … read the check in instructions before you get there. "
The price is SAR 1,313
SAR 2,392 total
includes taxes & fees
4 Nov - 5 Nov
Designer Oceanfront Retreat Featured in Architectural Digest ☀ Steps from Beach
Lg Suite for up to 8 ppl/1 floor
Terrace/patio

Lg Suite for up to 8 ppl/1 floor

9.0 out of 10, Wonderful, (14)
"Great place! Plenty of room, clean, and well kept. Very close to a ton of stuff to see and do. Highly recommend!"
The price is SAR 544
SAR 1,798 total
includes taxes & fees
29 Oct - 30 Oct
Lg Suite for up to 8 ppl/1 floor
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.
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Top Winchester Hotel Reviews

Midtown Hotel

Midtown Hotel

10/10 Excellent
"Came to Boston for a mother/daughter trip. The staff was so great & kind. The hotel is under renovations. We had a leak in our ceiling & the staff was more than accommodating. They got us into another room as soon as one was available. The hotel even comped us for the room! "
Elizabeth 3-night trip
Posted 11 hours ago
Midtown Hotel

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from SAR 800 to SAR 4,605 per night. These properties offer loads of space for the whole family at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winchester?
Take your pick of 184 condos in Winchester. No matter if you're traveling with the kids or planning a weekend escape with your buddies, Expedia will help you find the right space for your entire crew.
Why book your condo in Winchester with Expedia?
Booking a condo in Winchester is as simple as deciding on your travel dates and selecting an option that satisfies your needs. Seeking something upscale or budget friendly, or a stay that also features a laundry and kitchen? Use Expedia's search filters to further narrow your search results and find the ideal fit at the right price.