Search Winthrop Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Cottages in Winthrop

Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (59)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is ￥66,236
￥86,957 total
includes taxes & fees
Sep 2 - Sep 3
Lighthouse Lane
Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.
Property grounds

Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.

2.0 star property
10.0 out of 10, Exceptional, (14)
"Very relaxing. Beautiful property. Exactly as advertised!!"
Cozy 1 BR Maine lakeside cottage getaway with WiFi, laundry, and full kitchen.
Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!
Outdoor dining

Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!

9.2 out of 10, Wonderful, (70)
"We had an awesome week with our family very comfy and a great spot on Brettuns pond"
Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

9.0 out of 10, Wonderful, (2)
"Cozy cottage by the lake. Great scenery and wildlife. Great communication with host. "
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views
Private Dock on Messalonskee Lake: Cozy Cottage!
Property grounds

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great spot right on the lake, True to what was listed. The beds weren’t very comfortable but otherwise everything was great."
Private Dock on Messalonskee Lake: Cozy Cottage!
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit
Exterior

Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit

6.4 out of 10, (7)
"The listing stated there were upstairs tenants. Long story short, on Thanksgiving when they arrived home to me enjoying an outdoor fire, the accused me of using their firewood, I had brought my own. Then another night I left to do an activity with my kids and returned to not being able to park, due to them taking up three spaces with their truck. They were noisy every night until midnight and up every morning by 7a. In have no living family besides my kids and I was looking for a relaxing...
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit
Cozy lake house on Sabattus Pond 2 bed 1 Bath
Property grounds

Cozy lake house on Sabattus Pond 2 bed 1 Bath

9.2 out of 10, Wonderful, (11)
"Perfect place to stay for a weekend "
Cozy lake house on Sabattus Pond 2 bed 1 Bath
Family Friendly Updated Waterfront Cottage
Exterior

Family Friendly Updated Waterfront Cottage

9.2 out of 10, Wonderful, (31)
"My family and I enjoyed the cottage, the lake, and the surrounding area."
Family Friendly Updated Waterfront Cottage
Quiet - Romantic - Secluded Cottage on Lake
Exterior

Quiet - Romantic - Secluded Cottage on Lake

9.6 out of 10, Exceptional, (28)
"Great place to reconnect with yourself. "
Quiet - Romantic - Secluded Cottage on Lake
Lakeside Cottage On Tacoma lakes
Exterior

Lakeside Cottage On Tacoma lakes

Lakeside Cottage On Tacoma lakes
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks
Exterior

Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

10.0 out of 10, Exceptional, (43)
"Very clean and comfortable."
The price is ￥29,584
￥55,029 total
includes taxes & fees
Sep 16 - Sep 17
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks
Waterfront 2br/2ba cottage
Exterior

Waterfront 2br/2ba cottage

9.8 out of 10, Exceptional, (14)
"This property was wonderful. It had everything renters could ever need including an instant pot pressure cooker and excellent coffee machine that was stocked and ready to make good coffee. The cleanliness of the property was exceptional. The beds were very comfortable. We were in the area for cross country ski races and had a great stay. "
The price is ￥27,966
￥56,795 total
includes taxes & fees
Sep 1 - Sep 2
Waterfront 2br/2ba cottage
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Terrace/patio

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

9.2 out of 10, Wonderful, (17)
"Great location and wonderful hosts!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Family Cottage On Androscoggin Lake
Property grounds

Family Cottage On Androscoggin Lake

9.6 out of 10, Exceptional, (33)
"Great fishing from the dock, shallow for little children, kayak fun. The cottage was great for our family; shaded, clean, well provisioned."
Family Cottage On Androscoggin Lake
"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations
Outdoor dining

"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations

9.6 out of 10, Exceptional, (62)
"Great location. fishing was awesome!! Tiffany was so nice and accommodating We had a nice few days! very nice getaway!"
"Not-A-Pine Lane COTTAGE" is a family treasure enjoyed by generations
Unique Cottage
Exterior

Unique Cottage

10.0 out of 10, Exceptional, (28)
"The property was very nice meeting all our needs. The view of the lake from the gorgeous screened porch and the gas fire log were great! A highly recommed cottage! "
Unique Cottage
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
Terrace/patio

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

10.0 out of 10, Exceptional, (13)
"We loved your house. You made our stay amazing. We will certainly be back in '24."
The price is ￥61,673
￥122,574 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Keyes Cottage | Lakefront • Dock • Kayaks
Lakefront Maine House ~ 4 Mi to Colby College
House (4 Bedrooms) | Interior

Lakefront Maine House ~ 4 Mi to Colby College

3.0 star property
Lakefront Maine House ~ 4 Mi to Colby College
Private Dock on Messalonskee Lake: Cozy Cottage!
Cottage (2 Bedrooms) | Interior

Private Dock on Messalonskee Lake: Cozy Cottage!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
Private Dock on Messalonskee Lake: Cozy Cottage!
Lavender Haze Cottage in the Woods
Exterior

Lavender Haze Cottage in the Woods

9.2 out of 10, Wonderful, (5)
"We stayed here after our wedding in Vassalboro. The perfect getaway for the night "
Lavender Haze Cottage in the Woods
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

Center Street Value Inn

Center Street Value Inn

10/10 Excellent
"The ppl was very nice room looked very good "
Donna 2-night trip
Posted 8 hours ago
Center Street Value Inn

Frequently asked questions

Why book your cottage in Winthrop with Expedia?
We think a getaway should be a piece of cake, so if you're on the lookout for cottages in Winthrop at a nice price, Expedia has you covered. Keep the budget in check and opt for a cheap option surrounded by wilderness, or splurge on a luxury cottage to pamper your favorite people.
How can I find cheap cottages in Winthrop?
With Expedia's helpful filter tool, locating cheap cottages in Winthrop is a snap. To view accommodations that are friendly on the wallet, fine-tune your search results by star rating, budget and amenities.