Longmeadow Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Longmeadow

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (15)
"Excellent communication with owner, answered all questions immediately via text when we were onsite. Well maintained property with great basement for hanging out as a family. "
Massachusetts Vacation Rental w/ Deck

Treehouse | Countryside | Farm Animals | Fire Pit

9.6 out of 10, Exceptional, (21)
"My second time here and it honestly feels like a second home. The animals are friendly and so was Carmen! It's honestly a must, if you have a bucket list. Joseph was very helpful and thorough as a superhost. I highly recommend visiting! "
The price is AU$452
includes taxes & fees
10 Dec - 11 Dec
Treehouse | Countryside | Farm Animals | Fire Pit

Island Vibes Home

10.0 out of 10, Exceptional, (8)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is AU$264
includes taxes & fees
4 Dec - 5 Dec
PICON COZY

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

9.2 out of 10, Wonderful, (20)
"Brought the kids and grandkids to six flags. This rental was a short drive. We had a group of eight and everyone had plenty of room. The place was clean stocked and as advertised. If we are ever in the area again we will definitely stay again. "
The price is AU$843
includes taxes & fees
25 Nov - 26 Nov
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is AU$555
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Lakefront | King | PetsOK | W&D | Fire Pit | Kayak

8.8 out of 10, Excellent, (14)
"Beautiful house, with very artistic and historical finishes. The view is beautiful"
The price is AU$436
includes taxes & fees
4 Dec - 5 Dec
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak

The Creation Station is a cozy place so make yourself at home.

10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is AU$437
includes taxes & fees
26 Nov - 27 Nov
The Creation Station is a cozy place so make yourself at home.

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very good, (8)
"Eunice was great to work with, and the place was fantastic for our family of four going to six flags."
The price is AU$421
includes taxes & fees
25 Nov - 26 Nov
Thomas's Cozy Duplex - Centrally Located

Exquisite Downtown Loft Apartment

8.0 out of 10, Very good, (6)
"Will stay again"
Exquisite Downtown Loft Apartment

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

10.0 out of 10, Exceptional, (61)
"Went to the Big E for a few days, great location, 10-15 minute ride to the fair. Was perfect to come back and relax after a long day at the fair. Home was very clean and updated. Communication was great. Could use some pans that work with the cooktop. The bathroom setup was a little strange, you have to walk throught the master bedroom to get to the bathroom, so the second bedroom guest had to walk through our bedroom in the middle of the night to use the restroom. Ad states Oven, hot tub,...
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"Very nice and clean. Great location for proximity to our family"
Linny's Updated Lakeview Cottage - Cozy & Modern

Tastefully furnished repose home

6.0 out of 10, (3)
"The neighborhood is not safe at all. "
Tastefully furnished repose home

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (29)
"It was nice stay!"
The price is AU$495
includes taxes & fees
6 Dec - 7 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Welcome to Honey Spot!

9.8 out of 10, Exceptional, (27)
"House was extremely clean. Fully stocked. Host was very helpful. Would stay again."
Welcome to Honey Spot!

comfortable home away from home

8.8 out of 10, Excellent, (8)
"Great host and a great place really close to HFD and Pratt & Whitney."
comfortable home away from home

Large house with game-room, deck, bbq grill, basketball/volleyball nets.

9.8 out of 10, Exceptional, (8)
"We reserved this delightful house for a family gathering, and it was everything we'd hoped for and more. Lots of space for everyone, and terrific for entertaining - there's a spacious deck, a gaming area upstairs, and an entire basement for recreation (pool, table tennis, air hockey, or just relaxing). The kitchen had everything we needed and was thoughtfully laid out and equipped. The host was helpful and responded almost immediately to the few questions I had. And, the neighborhood and...
Large house with game-room, deck, bbq grill, basketball/volleyball nets.

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

9.6 out of 10, Exceptional, (4)
"This property appeared to be recently built. While the neighborhood is nice and appeared to be safe, there were not enough utensils for the 6 people in our party. I also requested the check-in code at least the night before we arrived and that did not happen. As of the morning we flew out to Hartford, I hadn't received the check in code...very frustrating. Also the only chairs to sit in were in the downstairs living room and kitchen. If you wanted to watch TV in a bedroom, your only option was...
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Trainmaster's Inn - Caboose

9.4 out of 10, Exceptional, (3)
"Husband is a railfan he was at the tracks several times a day"
The price is AU$495
includes taxes & fees
24 Nov - 25 Nov
Trainmaster's Inn - Caboose
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.
Don't see what you're looking for?
See all available properties in Longmeadow
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Longmeadow you may be interested in

The Capitol Hotel, Ascend Hotel Collection

3.0 star property
7.4 out of 10, Good, (943)
"Didn’t enjoy the fact that they charged $15 for parking."
The price is AU$133
includes taxes & fees
22 Dec - 23 Dec
The Capitol Hotel, Ascend Hotel Collection

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1227)
"Fun"
The price is AU$284
includes taxes & fees
25 Nov - 26 Nov
MGM Springfield

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2.0 star property
6.6 out of 10, (1428)
"I was told that there was 24/7 shuttle service from Bradley Int. Airport. I called from Minneapolis as I got onto my flight and confirmed that there was such service. To my shock, when I arrived at BDL, I called Days Inn and there was NO service. The night manager could barely speak into the phone but I understood her to say, "Take a taxi". It wasn't the terribile but I had had a long day of travel and to wait at 1am for a LYFT as there were no taxis."
The price is AU$126
includes taxes & fees
24 Nov - 25 Nov
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Longmeadow?

Yes, there are holiday rentals close to the most popular sights in Longmeadow, or you can select a more secluded option if you're looking for a relaxing stay. Longmeadow is known for its shopping and restaurants. Make sure you have time to check out the churches while you're in the area.

What are some of the best holiday rentals that Longmeadow has to offer?

PICON COZY: This holiday home rental outside of Longmeadow has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Longmeadow?

Choose from 4 Expedia holiday rentals in Longmeadow for a memorable holiday.

What can I see and do in Longmeadow?

Forest Park and Connecticut River are a couple of lovely local spots to get outside and enjoy nature. Six Flags New England and Titanic Museum are a couple of places you'll find in the wider area.

What are holiday rentals like in Longmeadow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longmeadow. Holiday rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family getaway.