
Holiday rentals in Winthrop
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Top-rated holiday rentals in Winthrop
Guests agree: these stays are highly rated for location, cleanliness and more.

Off-Grid Escape. Wood Fired Hot Tub, Snowshoes
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Room B with private entrance, bathroom & hot tub
Room B is a small (10’ x 10’) but cozy room with full size bed with luxury mattress and private bathroom (5’ x8’) with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

1820s Maine Cottage with Garden
Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

Designers Dream 1br Apt where class meets relax!!!
This Designers Dream 1br apartment is located in the quintessential small Maine town of Richmond. Open the door feast your eyes on this truly unique and beautiful spot and get ready to relax or explore! Richmond is home of Swan Island a great spot to explore via kayak or canoe or just grab the ferry! We're 45 min to all downtown Portland has to offer. We are an hour to Booth Bay Harbor and the beautiful botanical gardens. Popham beach is 45 min away, one of the most amazing beaches in state.

Maine lakehouse-Ice fishing, skiing, snowmobiling
Beautiful lake living & winter activities, 2.5 hours from Boston, 40 min. from Portland. Near skiing- 1:20 from Sunday River, 1:10 Pleasant Mtn., 1:05 Mount Abram Ski Area, 0:20 Lost Valley. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances. Minutes to Lewiston/Auburn - close to dining and stores. Well known ice fishing spot , cross-country skiing nearby too. Fire pit, great sunsets.

Jill's Place!
This is a brand new daylight basement airbnb with access to Cobeeseecontee Lake in Winthrop Me. 2 bdrm. 1 with a queen and 2nd with 2 twins. It is decorated with with white shiplap, beautiful hardwood floors and very light and bright. It is 160 ft from the lakeside where there is a very nice grassy area with lounge chairs, a dock, and a swimming area. 1 kayak and a peddle lboat included. 500 ft away from the Travis Mills restaurant "The White duck" 2 miles from the famous Cabin Masters!

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Welcome to the Brown House! Hallowell studio
Enjoy Hallowell and Central Maine while staying at our studio apartment. An easy walk to downtown Hallowell to shops, restaurants , and pubs. Take a walk on the Kennebec Rail Trail . A 15 minute drive to visit Maine Cabin Masters. Hour drive to Boothbay Harbor, Rockland, or Belfast. Studio is located above owners garage : separate entrance and off street parking. Included: linens, towels, TV, WiFi, single Keurig, microwave, toaster, college size dorm fridge, small cooler

Charming Cottage With Spectacular Water View
Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Hallowell Hilltop Home with Hot Tub & Sauna
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Cozy, Efficiency Apartment with Hot Tub
Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Secluded, cozy cabin nestled in the Maine woods
Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.
Popular amenities for Winthrop holiday rentals
Other great holiday rentals in Winthrop

Lighthouse Lane

Peaceful Private Room on the Nezinscot River

Charming waterfront camp on Maranacook Lake

Cozy Home Base

Dock + Kayaks: Annabessacook Lake Retreat!

Loon Haven

~ Brookhirst Farm ~ 3 Bedrooms, 2 Full Baths

WillowsAwake Winery Stay
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £122 | £133 | £135 | £135 | £174 | £175 | £178 | £185 | £167 | £185 | £147 | £133 |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Frequently Asked Questions
What are the most popular amenities for House Rentals in Winthrop?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 30 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do cabin rentals in Winthrop have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winthrop have wifi?
Absolutely! We offer over 30 house rentals with wifi in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winthrop?
Yes! Work meets play with ease at over 30 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Winthrop have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Winthrop?
Winthrop has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Winthrop?
Experience the best of Winthrop with our cabin rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Quick stats about holiday rentals in Winthrop

Total holiday rentals
Explore 70 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 2,130 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of Winthrop holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a patio Winthrop
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- Family-friendly rentals Winthrop
- House rentals Winthrop
- Rentals with lake access Winthrop
- Rentals with a kayak Winthrop
- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Belgrade Lakes Golf Club
- Willard Beach
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Wolfe's Neck Woods State Park
- Black Mountain of Maine
- Sunday River Golf Club
- Fox Ridge Golf Club
- The Camden Snow Bowl
- Hunnewell Beach
- Maine Maritime Museum
- Bradbury Mountain State Park
- Brunswick Golf Club
- Eaton Mountain Ski Resort
- Portland Museum of Art
- Titcomb Mountain
- Lost Valley Ski Area




