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Holiday Rentals in Southampton

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Holiday Rentals in Southampton

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

8.8 out of 10, Excellent, (5)
"Great property! Thank you for a wonderful stay."
The price is €336
includes taxes & fees
21 Jul - 22 Jul
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Charming Chicopee Getaway

The price is €275
includes taxes & fees
12 Aug - 13 Aug
Charming Chicopee Getaway

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.4 out of 10, (10)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

PICON COZY

7.6 out of 10, Good, (67)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is €143
includes taxes & fees
20 Jul - 21 Jul
PICON COZY

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (19)
"Our group had a wonderful time and we will not hesitate to book again in the future. The place was exceptionally clean, well appointed, and very comfortable. Overall it was a great experience! "
The price is €211
includes taxes & fees
20 Jul - 21 Jul
Easthampton Vacation Rental - Walk to Breweries!

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

9.6 out of 10, Exceptional, (31)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is €290
includes taxes & fees
31 Jul - 1 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (42)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

comfort, luxury, privacy

9.8 out of 10, Exceptional, (63)
"My wife and I were only there for one night but will definitely stay at this property again in the future, communication was quick and friendly and the apartment was clean and cozy!!!"
comfort, luxury, privacy

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

10.0 out of 10, Exceptional, (1)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
The price is €466
includes taxes & fees
21 Jul - 22 Jul
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (34)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"The house is so charming. Beautifully decorated and very clean, with everything you could need easy to find. Plenty of space for 8 people. The hosts are very helpful and communicative. Would definitely stay here again."
The price is €316
includes taxes & fees
27 Jul - 28 Jul
Big farmhouse in the foothills of the Berkshires

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.4 out of 10, Exceptional, (14)
"This was a sweet place to stay while we were in the area for a graduation. It is a beautiful little apartment with everything we needed, cozy and quiet, and Lucienne’s communications were clear and welcoming!"
The price is €187
includes taxes & fees
22 Jul - 23 Jul
Newly Built Barn Loft in Pioneer Valley

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is €147
includes taxes & fees
18 Jul - 19 Jul
HOMEY HOMEY

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (8)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (7)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Button's Modern Luxury Walkup Downtown Northampton

The price is €444
includes taxes & fees
22 Jul - 23 Jul
Button's Modern Luxury Walkup Downtown Northampton

Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

7.0 out of 10, Good, (8)
"The house was very clean. It was difficult finding the rental and required calling the host. There’s a bbq grill but no grill equipment like tongs, spatula or scraper, the outside fire table did not work and the back yard had trash on the ground. The kitchen hot mitts were crusty and dirty, fixtures were falling off in the bathroom and the place needs another mirror for getting ready"
Mins from MGM, Downtown springfield, Mercy and Baystate Medical center.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (216)
"I love this place! It's been beautifully remodeled and is very comfortable. I would love to visit when it's warmer, but it's very cozy in the snow. I can't wait to come back with my kids. "
Peace and quiet on the lake

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (4)
"Its was quite and peaceful, Judy was very easy to communicate with. We would stay here again"
Lake Congamond Cozy Stylish Comfortable House

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

10.0 out of 10, Exceptional, (68)
"Great stay with good amenities. Thanks for the tea!"
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
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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Frequently asked questions

Are there holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, or you can select a more secluded option if you're looking for a relaxing stay. Southampton is known for its restaurants and shopping.

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

Bring Your Pet & Visit Springfield: Westfield Home: This holiday home rental outside of Southampton offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What can I see and do in Southampton?

Conant Park and Southampton Center Historic District are a couple of lovely local spots to get outside and enjoy nature. Southampton Town Hall and Edwards Public Library are other places to visit while you're in town.

What are holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.