A calm lake surrounded by trees and a clear sky.

Webster Vacation Rentals

Dates

November 2026

December 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Webster vacation rentals

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. The Tree House at Underhill Hollow

Thompson

Zachary P.

￥29,421 total

includes taxes & fees

Nov 11 - Nov 12

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. Wizard's Roost at Underhill Hollow

North Grosvenordale

Elizabeth G.

￥28,510 total

includes taxes & fees

Nov 11 - Nov 12

A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

3. SteamPunk Bunk House and Intergalactic Way Station

Thompson

Pauline S.

￥28,510 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a wooden bed, large windows, and a view of greenery outside.

4. Rustic Farmette Studio with Hot Tub & Pool

Thompson

Lynn J.

￥58,321 total

includes taxes & fees

Nov 11 - Nov 12

A modern interior with a dining area, kitchen, and seating space.

5. 1 King Bed | Non-Smoking, Micfridge

Putnam

Anonymous traveler

￥15,913 total

includes taxes & fees

Nov 11 - Nov 12

A two-story house with a front porch, stone steps, and a driveway.

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

Putnam

Dan M.

￥31,999 total

includes taxes & fees

Nov 11 - Nov 12

A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Sturbridge

Lynn M. T.

￥19,705 total

includes taxes & fees

Nov 11 - Nov 12

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

8. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Sturbridge

Trish N.

￥58,063 total

includes taxes & fees

Nov 11 - Nov 12

A house with a white porch, a black door, and a window with a white frame.

9. Cozy 1-bedroom cottage in serene Pomfret.

Pomfret

Aaron H.

￥41,878 total

includes taxes & fees

Nov 17 - Nov 18

A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

10. Clean & Cozy Private-3 floor_R 2

Union HIll

Ekaterina

￥16,705 total

includes taxes & fees

Nov 11 - Nov 12

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

Worcester

Sierra M.

￥54,939 total

includes taxes & fees

Nov 11 - Nov 12

A wooden cabin with a glass upper floor, surrounded by a forest.

12. Dove Cabin up in the Trees

Holland

Zachary C.

￥39,114 total

includes taxes & fees

Nov 11 - Nov 12

A lakeside cabin with a deck, a dock, and a small docked boat.

13. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Sturbridge

Anonymous traveler

￥74,882 total

includes taxes & fees

Nov 11 - Nov 12

A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

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

Franklin Plantation

Taisha M.

￥49,517 total

includes taxes & fees

Nov 11 - Nov 12

A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Woodstock

Emma S.

￥97,941 total

includes taxes & fees

Nov 11 - Nov 12

A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

16. Newly Refreshed 3bd Spacious Unit Minutes from 290

Franklin Plantation

Anonymous traveler

￥50,969 total

includes taxes & fees

Nov 12 - Nov 13

A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

17. Lake House in Sturbridge w/All the Views!

Sturbridge

Mike T.

A kitchen with wooden cabinets, a window with a view, a vase with flowers, and framed pictures on the windowsill.

18. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

Millbury

Roberto A G.

￥55,113 total

includes taxes & fees

Nov 11 - Nov 12

A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

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

Main South

"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...

Elyse D.

￥48,918 total

includes taxes & fees

Dec 1 - Dec 2

A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

20. Clifford Luxury Retreat 3BR Self Check In Home

Northbridge

Martin G.

￥69,853 total

includes taxes & fees

Nov 11 - Nov 12

View all properties

Find vacation rentals that suit your style

Top Webster Hotel Reviews

An outdoor patio area with seating, tables, and decorative lights.

Wellsworth Hotel

Southbridge

10/10 Excellent

Brian

A hotel entrance with a covered walkway, columns, and a brick facade.

Holiday Inn Express & Suites Sturbridge by IHG

Sturbridge

10/10 Excellent

Tracy

A hotel with a parking lot, a covered entrance, and a brick facade.

Holiday Inn Express Hotel & Suites Auburn by IHG

Auburn

10/10 Excellent

bernard

A hotel with a covered patio, a stone fountain, and a brick pathway.

Comfort Inn & Suites Sturbridge - Brimfield

Sturbridge

10/10 Excellent

Jim

A hotel entrance with a covered walkway, a parking area, and a well-lit building facade.

Hampton Inn Auburn

Auburn

10/10 Excellent

A bunch of stuff in the surrounding area to eat and locations not to far away from many different places to do stuff. Everything was clean, staff was always nice. Free breakfast was simple but nice and had little something for everyone. The pools been down for a long time but for me personally not really a deal breaker. Simple clean room with a place to sleep while going out on daily adventures with the wife. Ive stayed in some really gross places traveling doing sports and other events so...

Adam

A Fairfield Inn & Suites by Marriott hotel with a covered entrance and landscaped surroundings.

Fairfield Inn & Suites by Marriott Worcester Auburn

Auburn

10/10 Excellent

Anonymous traveler

A white colonial-style house with a symmetrical facade, a central entrance, and a well-maintained garden with colorful flowers.

Publick House Historic Inn and Country Motor Lodge

Sturbridge

10/10 Excellent

Suzanne

A Comfort Inn & Suites hotel with a well-maintained garden and a clear view of the building's entrance.

Comfort Inn & Suites Dayville - Killingly Industrial Park

Dayville

10/10 Excellent

Our first time at this location, we stayed here 2 nights while attending the May 2016 Brimfield markets. Easy on/off route 395 in a quiet area by an industrial park and rr tracks. About a 30 minute scenic drive to Brimfield (395N to 131 to 20). Although the hotel is 18 years old, the rooms were redone 2 years ago giving it a very modern appearance. The breakfast buffet was included (bacon, eggs, fresh fruit, yogart, oj, apple juice, great coffee, delicious blue berry waffles). Fresh baked...

peggy

A large building with multiple windows and a well-maintained garden with various plants and flowers.

Scottish Inn Sturbridge

Sturbridge

10/10 Excellent

Dale

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

Hampton Inn & Suites Worcester

Worcester

10/10 Excellent

Tammy

A modern hotel dining area with a long table, chairs, and a television on the wall.

Hampton Inn Boston - Westborough

Westborough

10/10 Excellent

Paul

An outdoor seating area with colorful striped sofas and chairs, a central fire pit, and a covered patio with string lights.

Home2 Suites by Hilton Smithfield, RI

Smithfield

10/10 Excellent

Lori

Find out more about Webster

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

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

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

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 Dudley Hill Golf Club at 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.

Webster Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Webster vacation rentals

1. The Tree House at Underhill Hollow

2. Wizard's Roost at Underhill Hollow

3. SteamPunk Bunk House and Intergalactic Way Station

4. Rustic Farmette Studio with Hot Tub & Pool

5. 1 King Bed | Non-Smoking, Micfridge

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

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

8. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

9. Cozy 1-bedroom cottage in serene Pomfret.

10. Clean & Cozy Private-3 floor_R 2

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

12. Dove Cabin up in the Trees

13. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

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

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

16. Newly Refreshed 3bd Spacious Unit Minutes from 290

17. Lake House in Sturbridge w/All the Views!

18. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

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

20. Clifford Luxury Retreat 3BR Self Check In Home

Find vacation rentals that suit your style

Top Webster Hotel Reviews

Wellsworth Hotel

10/10 Excellent

Find out more about Webster

Frequently Asked Questions

Can I find vacation rentals in Webster?

What are some of the best vacation rentals in Webster?

How many vacation rentals will I find in Webster?

What can I see and do in Webster?

What are vacation rentals like in Webster?