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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Webster vacation rentals

Interior

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is SAR 473
SAR 731 total
includes taxes & fees
16 Aug - 17 Aug
The Tree House at Underhill Hollow
Exterior

2. 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 SAR 473
SAR 709 total
includes taxes & fees
23 Aug - 24 Aug
Wizard's Roost 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, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is SAR 473
SAR 709 total
includes taxes & fees
17 Aug - 18 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior

4. 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 SAR 571
SAR 970 total
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior detail

5. 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 SAR 920
SAR 1,178 total
includes taxes & fees
27 Aug - 28 Aug
Cozy 1-bedroom cottage in serene Pomfret.
Interior

6. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is SAR 188
SAR 499 total
includes taxes & fees
14 Aug - 15 Aug
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

7. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (34 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is SAR 659
SAR 978 total
includes taxes & fees
16 Aug - 17 Aug
Dove Cabin up in the Trees
Exterior

8. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is SAR 394
SAR 752 total
includes taxes & fees
26 Aug - 27 Aug
The Carriage House at Chaprae Hall
1 bedroom, internet, bed sheets

9. 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 SAR 301
SAR 430 total
includes taxes & fees
16 Aug - 17 Aug
Clean & Cozy Private room - 3 floor_R 1
Smart TV

10. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is SAR 1,021
SAR 2,071 total
includes taxes & fees
7 Sep - 8 Sep
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Interior

11. 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 SAR 695
SAR 1,363 total
includes taxes & fees
13 Sep - 14 Sep
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Exterior

12. 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 SAR 859
SAR 990 total
includes taxes & fees
18 Aug - 19 Aug
Cottage by the Castle – Downtown Spencer
Interior

13. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
The price is SAR 654
SAR 1,497 total
includes taxes & fees
16 Aug - 17 Aug
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Outdoor dining

14. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is SAR 604
SAR 1,265 total
includes taxes & fees
17 Aug - 18 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV

15. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (4 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is SAR 582
SAR 1,229 total
includes taxes & fees
28 Aug - 29 Aug
Large 3BD 1st Floor Apartment Minutes from 290
Dining

16. 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 SAR 792
SAR 1,639 total
includes taxes & fees
25 Aug - 26 Aug
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Dining

17. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (15 reviews)
"Very comfortable and relaxing on the inside with beautiful surroundings and hiking trails right on the property. Exactly what we wanted for a get-away and such close proximity to the zoo where we attended a wedding."
United States
Tammie K.
The price is SAR 805
SAR 980 total
includes taxes & fees
7 Sep - 8 Sep
Zen Inspired Retreat with Private Forest Trails
Property grounds

18. 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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is SAR 591
SAR 757 total
includes taxes & fees
18 Aug - 19 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Interior

19. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is SAR 625
SAR 1,004 total
includes taxes & fees
16 Aug - 17 Aug
Spacious, unique barn with beautiful views.
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is SAR 1,877
SAR 3,033 total
includes taxes & fees
6 Sep - 7 Sep
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

8/10 Good
"The lamp did not work, may have e just needed a new bulb. rm 103 Also, the shower needs to be looked at for the pressure & also the drainage of the tub. Small details, but could be a quick fix"
Donna 1-night trip
Posted 1 hour ago
Publick House Historic Inn and Country Motor Lodge

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.