A calm lake surrounded by trees and a clear sky.

Webster Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Webster vacation rentals

Exterior

1. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is AED 463
AED 690 total
includes taxes & fees
30 Aug - 31 Aug
Wizard's Roost at Underhill Hollow
Interior

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (41 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AED 463
AED 715 total
includes taxes & fees
29 Aug - 30 Aug
The Tree House at Underhill Hollow
Property grounds

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 690 total
includes taxes & fees
30 Aug - 31 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior detail

4. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is AED 900
AED 1,163 total
includes taxes & fees
10 Sep - 11 Sep
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

5. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (35 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is AED 645
AED 957 total
includes taxes & fees
29 Aug - 30 Aug
Dove Cabin up in the Trees
Exterior

6. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (6 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is AED 536
AED 930 total
includes taxes & fees
2 Sep - 3 Sep
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Interior

7. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is AED 191
AED 295 total
includes taxes & fees
30 Aug - 31 Aug
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Terrace/patio

8. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved the house and the grounds looking over the lake. The house was very clean and had everything we needed. The yard, front and back were really lovely. The backyard overlooked Quasset Lake. We were fortunate to enjoy pleasant weather. The beds were comfortable. The living room and kitchen overlooked the lake with a large deck off the area. There is shade available over the deck if the sun gets too hot. We were there only for the weekend, but had a fabulous time."
United States
Gayle B.
The price is AED 1,653
AED 2,730 total
includes taxes & fees
30 Aug - 31 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

9. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is AED 595
AED 1,231 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Coffee/tea maker, fridge, microwave, oven

10. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location"
United States
Harmony F.
The price is AED 1,010
AED 1,900 total
includes taxes & fees
30 Aug - 31 Aug
Spacious 4-bedroom with four and half bathrooms
Coffee/tea maker, fridge, microwave, stovetop

11. FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161

FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
Worcester
8.0 out of 10, Very Good, (5 reviews)
"Easy in and out when in town. Clean and efficient property. "
United States
Diane S.
The price is AED 543
AED 1,433 total
includes taxes & fees
30 Aug - 31 Aug
FREE Parking & Renovated 4BR Stay 1st-floor Apt Near Clark Uni, Laundry + AC 161
Iron/ironing board, WiFi, bed sheets

12. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
The price is AED 628
AED 893 total
includes taxes & fees
31 Aug - 1 Sep
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Property grounds

13. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (9 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is AED 612
AED 782 total
includes taxes & fees
1 Sep - 2 Sep
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Dining

14. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (88 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,745
AED 2,828 total
includes taxes & fees
1 Sep - 2 Sep
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Dining

15. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.6 out of 10, Exceptional, (4 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is AED 632
AED 1,429 total
includes taxes & fees
30 Aug - 31 Aug
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Exterior

16. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AED 841
AED 969 total
includes taxes & fees
10 Sep - 11 Sep
Cottage by the Castle – Downtown Spencer
Smart TV

17. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (52 reviews)
"Convenient location for our stay. Great communication by host. Bedrooms were spacious and clean. Large driveway for plenty of parking. Convenient to many shopping options and beautiful park close by. "
United States
Theresa L.
The price is AED 625
AED 1,149 total
includes taxes & fees
31 Aug - 1 Sep
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Dining

18. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is AED 788
AED 959 total
includes taxes & fees
7 Sep - 8 Sep
Zen Inspired Retreat with Private Forest Trails
1 bedroom, internet, bed sheets

19. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
2.0 out of 10, (1 review)
The price is AED 294
AED 421 total
includes taxes & fees
30 Aug - 31 Aug
Clean & Cozy Private room - 3 floor_R 1
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 Webster Hotel Reviews

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Tammy at the front desk was wonderful. Convenient location. My granddaughter called it Bougie, I guess that means fancy in 11 year old language."
Candace 2-night trip
Posted 16 hours ago
Wellsworth Hotel

Frequently asked questions

Can I find vacation rentals in Webster?

Yes, we have vacation rentals in Webster near Mohegan Bowl, or you can go with a more secluded option if you'd like a relaxing place to stay. Webster is known for its lake views and seafood restaurants. Make sure you have time to check out the entertainment choices while you're in the area.

What are some of the best vacation rentals in Webster?

3-bedroom house on Webster Lake with amazing views, beach and boat launch access: This Webster vacation home rental is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Another good choice for your trip to Webster is Webster Lake - One Home -Two Apartments.

How many vacation rentals will I find in Webster?

Expedia has 5 vacation rentals for your stay in Webster.

What can I see and do in Webster?

Cultural attractions include Indian Ranch, whereas Mohegan Bowl is just one of the family-friendly sights. Lake Chaubunagungamaug and Nichols College are a couple of places you'll find in the larger area.

What are vacation rentals like in Webster?

Vacation rentals are private properties you can book for a few days or a quick weekend in Webster. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.