Raymond Vacation Rentals

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Raymond vacation homes

A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

1. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is CA $318
CA $359 total
includes taxes & fees
Nov 18 - Nov 19
Cozy 2-bedroom house with shared beach access to Sebago Lake
A modern kitchen with a wooden dining table, a ceiling fan, and a view of the outdoors.

2. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is CA $346
CA $391 total
includes taxes & fees
Nov 18 - Nov 19
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
A lakeside property with a dock, inflatable raft, and a house with a balcony.

3. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (19 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is CA $283
CA $1,062 total
includes taxes & fees
Nov 9 - Nov 10
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
A modern kitchen with a bar area, wooden ceiling, and skylights.

4. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (10 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is CA $267
CA $480 total
includes taxes & fees
Nov 18 - Nov 19
The Barnhouse with hot tub
A covered porch with a view of a lake and trees.

5. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is CA $283
CA $920 total
includes taxes & fees
Nov 15 - Nov 16
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A modern cabin with a large glass facade, a hot tub, and wooden steps leading to the entrance.

6. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Naples
9.8 out of 10, Exceptional, (9 reviews)
"Fantastic home! We had a great time here and look forward to booking again."
United States
Gina P.
The price is CA $668
CA $1,042 total
includes taxes & fees
Nov 15 - Nov 16
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
A rustic room with a wooden ceiling, a hot tub, a black leather chair, and a small table with a flag.

7. Ell Suite walk to town beach

Ell Suite walk to town beach
Bridgton
8.8 out of 10, Excellent, (3 reviews)
"Great spot as advertised "
United States
mark l.
The price is CA $97
CA $189 total
includes taxes & fees
Nov 9 - Nov 10
Ell Suite walk to town beach
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is CA $152
CA $484 total
includes taxes & fees
Nov 9 - Nov 10
Quiet Spot in lovely Freeport neighborhood
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

9. Family, friends, Gathering

Family, friends, Gathering
Standish
8.0 out of 10, Very good, (2 reviews)
"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."
United States
Logan R.
The price is CA $1,017
CA $2,204 total
includes taxes & fees
Nov 12 - Nov 13
Family, friends, Gathering
A covered wooden deck with a view of a building's exterior.

10. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
7.6 out of 10, Good, (4 reviews)
"Overall all nice stay. Thank you"
United States
Hope T.
The price is CA $177
CA $460 total
includes taxes & fees
Nov 9 - Nov 10
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A loft-style bedroom with a sloped ceiling, a ceiling fan, a bed, a desk, and a kitchenette.

11. Peaceful Barn Loft near Sebago Lake and Conway, NH

Peaceful Barn Loft near Sebago Lake and Conway, NH
Hiram
The price is CA $191
CA $273 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful Barn Loft near Sebago Lake and Conway, NH
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

12. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is CA $202
CA $651 total
includes taxes & fees
Nov 11 - Nov 12
Fully Updated Airy Historic Home in South Freeport
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

13. Newly Renovated Luxury House with Game Room

Newly Renovated Luxury House with Game Room
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is CA $463
CA $1,102 total
includes taxes & fees
Nov 9 - Nov 10
Newly Renovated Luxury House with Game Room
Private kitchen

14. Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.2 out of 10, Wonderful, (5 reviews)
"The Manor Suite was cozy and charming. It was walking distance from restaurants and shops. I would have loved to stay longer to explore the area.I hope to stay there again if I return to Bridgton next summer."
United States
Jennifer
The price is CA $138
CA $238 total
includes taxes & fees
Nov 23 - Nov 24
Manor Suite,cozy newly renovated,downtown & beach
A view through a window of a lake surrounded by trees and a small house.

15. Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Bridgton
10.0 out of 10, Exceptional, (67 reviews)
"This was our second stay at Windsor Cottage, and it was just as wonderful as the first! The cottage is always spotless, beautifully furnished, and truly feels like a home away from home. We love the lake access, the pet-friendly accommodations, and being just minutes from downtown Bridgton. We can’t wait to come back again!"
United States
Cortney C.
The price is CA $212
CA $500 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
A compact living space with a bed, washing machine, and refrigerator.

16. The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi

The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi
Bridgton
10.0 out of 10, Exceptional, (3 reviews)
"Host was amazing. Great spot in Bridgton!"
Canada
Joshua
The price is CA $225
CA $530 total
includes taxes & fees
Nov 9 - Nov 10
The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

17. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (17 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is CA $585
CA $1,087 total
includes taxes & fees
Nov 22 - Nov 23
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A hallway with a wooden floor, a staircase with a wooden handrail, and a view into a dining area with a kitchen in the background.

18. Winter Farmhouse - Hot Tub, Sauna & Ski Day Trips

Winter Farmhouse - Hot Tub, Sauna & Ski Day Trips
Harrison
The price is CA $456
CA $1,042 total
includes taxes & fees
Nov 17 - Nov 18
Winter Farmhouse - Hot Tub, Sauna & Ski Day Trips
A white door with a window, two potted plants, and a welcome mat.

19. Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!

Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!
Bridgton
10.0 out of 10, Exceptional, (4 reviews)
"The house was clean and beautiful! The host made sure we had everything we needed including items for our doggie. We would definitely recommend staying here!"
United States
Jacqueline R.
The price is CA $410
CA $813 total
includes taxes & fees
Nov 9 - Nov 10
Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

20. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is CA $134
CA $493 total
includes taxes & fees
Nov 9 - Nov 10
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
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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Learn more about Raymond

Spend summer days boating on Sebago Lake, where you can rent kayaks or join locals fishing for bass. Explore the trails at Raymond Beach or visit nearby Poland Spring's historic water museum for a refreshing Maine experience.

See all hotels in Raymond
A misty lake at sunrise with a wooden dock and a tree in the foreground.

Top reviews in Raymond

A modern hotel lobby with a long reception desk, comfortable seating, and a large flat-screen TV mounted on the wall.
Hampton Inn Oxford

Hampton Inn Oxford

Hampton Inn Oxford
Oxford

10/10 Excellent

Nice hotel Friendly staff Good breakfast
Canada
Marco
Reviewed July 13, 2026
Hampton Inn Oxford

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