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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Southampton vacation rentals
1. The Creation Station is a cozy place so make yourself at home.
The Creation Station is a cozy place so make yourself at home.Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
Paula
$237 nightly
The price is $265
Nov 5 - Nov 6
Total with taxes and fees
2. Modern Studio Ideal for Traveling Professionals
Modern Studio Ideal for Traveling ProfessionalsHolyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
Kebreab H.
$194 nightly
The price is $217
Nov 8 - Nov 9
Total with taxes and fees
3. Work, Play & Stay! Apt Near Holyoke Medical Center
Work, Play & Stay! Apt Near Holyoke Medical CenterHolyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
Yvonne A.
$266 nightly
The price is $297
Nov 5 - Nov 6
Total with taxes and fees
4. Townhouse with Pool Table - Renovated w/ King Bed
Townhouse with Pool Table - Renovated w/ King BedChicopee
10.0 out of 10, Exceptional, (18 reviews)
"Comfortable stay"
Nicholas B.
$370 nightly
The price is $420
Nov 9 - Nov 10
Total with taxes and fees
5. Modern Studio Ideal for Traveling Professionals
Modern Studio Ideal for Traveling ProfessionalsHolyoke
$208 nightly
The price is $233
Nov 8 - Nov 9
Total with taxes and fees
6. Cozy Home in Holyoke with 3 bedrooms
Cozy Home in Holyoke with 3 bedroomsHolyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
Grant J.
$307 nightly
The price is $343
Dec 1 - Dec 2
Total with taxes and fees
7. Button's Modern Luxury Walkup Downtown Northampton
Button's Modern Luxury Walkup Downtown NorthamptonNorthampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
AMY
$426 nightly
The price is $476
Nov 17 - Nov 18
Total with taxes and fees
8. Cozy 2-bedroom apartment in Chicopee
Cozy 2-bedroom apartment in ChicopeeChicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
Christopher P.
$189 nightly
The price is $214
Nov 10 - Nov 11
Total with taxes and fees
9. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (155 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
Dale B.
$327 nightly
The price is $346
Nov 5 - Nov 6
Total with taxes and fees
10. Charming, updated 3 bedroom farmhouse farm stay.
Charming, updated 3 bedroom farmhouse farm stay.Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
Nancy M.
$412 nightly
The price is $436
Nov 5 - Nov 6
Total with taxes and fees
11. Penthouse overlooking downtown Amherst!
Penthouse overlooking downtown Amherst!Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
Mike S.
$433 nightly
The price is $484
Dec 1 - Dec 2
Total with taxes and fees
12. Cozy First Floor Apartment. Located in a quiet neighborhood.
Cozy First Floor Apartment. Located in a quiet neighborhood.Chicopee
9.6 out of 10, Exceptional, (14 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
Morrris
$268 nightly
The price is $304
Nov 30 - Dec 1
Total with taxes and fees
13. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six FlagsWest Springfield
10.0 out of 10, Exceptional, (1 review)
"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...
Jaimie F.
$278 nightly
The price is $318
Nov 9 - Nov 10
Total with taxes and fees
14. Newly Built Barn Loft in Pioneer Valley
Newly Built Barn Loft in Pioneer ValleyBelchertown
9.6 out of 10, Exceptional, (39 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
Nora M.
$216 nightly
The price is $228
Nov 5 - Nov 6
Total with taxes and fees
15. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
$247 nightly
The price is $276
Nov 9 - Nov 10
Total with taxes and fees
16. Serene 1-bedroom suite on 75 acre horse property
Serene 1-bedroom suite on 75 acre horse propertyBelchertown
10.0 out of 10, Exceptional, (40 reviews)
"Not your average stay! This place is super cool!!"
Wayne B.
$244 nightly
The price is $258
Nov 30 - Dec 1
Total with taxes and fees
17. 1 King Bed|Smoking, Micfridge
1 King Bed|Smoking, MicfridgeEnfield
10.0 out of 10, Exceptional, (5 reviews)
$68 nightly
The price is $79
Nov 5 - Nov 6
Total with taxes and fees
18. Cozy 2-bedroom apartment with movie theater.
Cozy 2-bedroom apartment with movie theater.Agawam
9.0 out of 10, Wonderful, (2 reviews)
"cute place, a bit humid and no AC control but the movie room is cool"
London R.
$285 nightly
The price is $318
Nov 8 - Nov 9
Total with taxes and fees
19. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
Brian C.
$320 nightly
The price is $357
Nov 5 - Nov 6
Total with taxes and fees
20. Modern Victorian 3BR 2BA Apt with Parking
Modern Victorian 3BR 2BA Apt with ParkingMcKnight
10.0 out of 10, Exceptional, (3 reviews)
"This is a beautiful old Victorian home. Very well maintained and very well appointed. The hosts are attentive and respond to questions promptly. The house was well stocked with all essentials Highly recommended."
Brandi S.
$628 nightly
The price is $713
Nov 5 - Nov 6
Total with taxes and fees
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
Fairfield Inn & Suites Springfield Holyoke
Fairfield Inn & Suites Springfield HolyokeHolyoke
10/10 Excellent
This hotel is great! The location is right off the highway, making it convenient to get to many areas quickly, using I91 or Riverdale Rd.
Breakfast is good, standard hotel food, but fresh. Hot coffee, tea, cocoa available all day and night in the lobby.
The lobby is big and a nice area to sit and visit or to just get out of your room for a while.
The mall is down the street, and Cracker Barrel, is behind the hotel, McDonalds, and Dunkin’ Donuts in front off.
We stay here every time we are in...
Diane
