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Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Southampton

Our top choices for Southampton vacation rentals

Tiny Home with AC and WiFi in lovely Ludlow
1 bedroom, WiFi, bed sheets

Tiny Home with AC and WiFi in lovely Ludlow

9.0 out of 10, Wonderful, (6)
The price is ￥11,757
￥22,276 total
includes taxes & fees
Oct 10 - Oct 11
Tiny Home with AC and WiFi in lovely Ludlow
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Terrace/patio

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (223)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (14)
"Great property! Thank you for a wonderful stay."
The price is ￥24,109
￥50,867 total
includes taxes & fees
Oct 6 - Oct 7
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

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

9.8 out of 10, Exceptional, (36)
"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 ￥26,155
￥45,375 total
includes taxes & fees
Sep 30 - Oct 1
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (200)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Fridge, microwave, oven, stovetop

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (23)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (25)
"Check in was easy. This met all of our needs. "
The price is ￥56,410
￥102,154 total
includes taxes & fees
Oct 1 - Oct 2
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
HOMEY HOMEY

HOMEY HOMEY

3.0 out of 10, (4)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
The price is ￥10,628
￥24,617 total
includes taxes & fees
Sep 26 - Sep 27
HOMEY HOMEY
3-bedroom house in perfect Springfield with WiFi, AC
TV

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
"Every question we had was quickly answered. The house was comfortable for us. Only a small hiccup in getting the door to lock when we left."
3-bedroom house in perfect Springfield with WiFi, AC
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
comfort, luxury, privacy
Fridge, microwave, oven, stovetop

comfort, luxury, privacy

9.8 out of 10, Exceptional, (71)
"The stay was very peaceful and the host were very helpful in terms of communication "
comfort, luxury, privacy
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
The price is ￥16,668
￥42,537 total
includes taxes & fees
Oct 21 - Oct 22
Charming Chicopee Getaway
Newly Beautiful renovated first floor apartment getaway
Fridge, microwave, oven, stovetop

Newly Beautiful renovated first floor apartment getaway

8.0 out of 10, Very Good, (2)
"We had an amazing time. This property was easy to find and very close to aloy of restaurants and shops! We had amazing chinese food! The apartment felt very homey. I love that it wasnt echo-y like past places I have stayed! I met Rose, the host, and she was super nice. She was very responsive and explained everything I needed to know before I arrived at the property. Also she lives near by and can address any problems or concerns you may have. The photography on the walls were gorgeous, the...
The price is ￥24,779
￥50,738 total
includes taxes & fees
Oct 1 - Oct 2
Newly Beautiful renovated first floor apartment getaway
Charming 3 bed/2 bath town home with gorgeous back yard
Property grounds

Charming 3 bed/2 bath town home with gorgeous back yard

9.8 out of 10, Exceptional, (12)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
The price is ￥67,753
￥85,071 total
includes taxes & fees
Sep 26 - Sep 27
Charming 3 bed/2 bath town home with gorgeous back yard
PICON COZY
Smart TV

PICON COZY

7.4 out of 10, Good, (69)
"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 ￥11,162
￥25,327 total
includes taxes & fees
Oct 20 - Oct 21
PICON COZY
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is ￥29,764
￥53,169 total
includes taxes & fees
Sep 28 - Sep 29
Big farmhouse in the foothills of the Berkshires
Amherst, Perfect Location, UMass, Smith, MHC!
Outdoor dining

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (17)
"Everything was clean and comfortable. It was a perfect getaway."
Amherst, Perfect Location, UMass, Smith, MHC!
Cozy Home in Holyoke with 3 bedrooms
Terrace/patio

Cozy Home in Holyoke with 3 bedrooms

9.6 out of 10, Exceptional, (9)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
The price is ￥19,189
￥47,816 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Home in Holyoke with 3 bedrooms
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 Southampton Hotel Reviews

Quality Inn West Springfield

Quality Inn West Springfield

10/10 Excellent
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
Danielle 1-night trip
Posted 2 days ago
Quality Inn West Springfield

Find out more about Southampton

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Southampton
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

Look no further and take a look at our great range of rental properties in Southampton!

Frequently asked questions

Are there vacation rentals in Southampton?

Yes, we give you a choice of vacation rentals where you'll be just 14.4 mi (23.1 km) from Six Flags New England, providing a more remote option if you'd like a quiet spot to stay. Southampton is known for its restaurants and shopping.

What's the top vacation rental in Southampton?

Tiny Home with AC and WiFi in lovely Ludlow: This vacation home rental near Southampton has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Southampton?

Conant Park and Pulaski Park 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 vacation rentals like in Southampton?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Southampton. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip.